CN102659856A - Preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose - Google Patents
Preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose Download PDFInfo
- Publication number
- CN102659856A CN102659856A CN2012101045585A CN201210104558A CN102659856A CN 102659856 A CN102659856 A CN 102659856A CN 2012101045585 A CN2012101045585 A CN 2012101045585A CN 201210104558 A CN201210104558 A CN 201210104558A CN 102659856 A CN102659856 A CN 102659856A
- Authority
- CN
- China
- Prior art keywords
- reaction
- benzoyl
- ribofuranose
- ethanoyl
- preparation technology
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
The invention relates to the technical field of chemical synthesis, and especially relates to a preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, which comprises a glycosilation reaction, a benzoylation reaction and an acetylation reaction. According to the invention, the low temperature glycosilation reaction is carried out at 0-5DEG C, so the generation of a pyranose ring is effectively reduced; the benzoylation reaction is carried out through adopting an inorganic weak base, so the raw material cost, and contents of nitrogen-containing organic matters in process wastewater are reduced; a cosolvent is added to an acetylation reaction system, so the solidification of glacial acetic acid is effectively inhibited, the fluidity of the reaction system is improved, and stirring can fully perform effects, and is in favor of smooth carrying-out of the reaction. The whole preparation technology which has the advantages of simple operation, high product yield, low cost, and low contents of the nitrogen-containing organic matters in the wastewater is suitable for industrialized production.
Description
Technical field
The present invention relates to chemosynthesis technical field, 1-O-ethanoyl-2,3 especially, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose.
Background technology
The non-natural nucleoside compounds is the analogue of natural nucleus glycoside compounds; The effect of mixing the spurious with the genuine is arranged in vivo; Can disturb or directly act on the metabolic process of nucleic acid; The life of blocking protein and nucleic acid is synthetic, thereby this compounds has important status in antiviral and anti-tumor chemotherapeutic medicine.Along with the quickening of this compounds research and development speed, the non-natural nucleoside compounds becomes the important means that people conquer germ, virus and cancer gradually.
The common structure characteristics of nucleoside compound are mainly to be made up of glycosyl and base; 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose are important glycosyl raw materials; Can be used for synthesizing multiple nucleoside medicine, for example Clofarabine, Azacitidine etc.1-O-ethanoyl-2,3, the synthetic route of 5-three-O-benzoyl--β-D-ribofuranose has three; Being starting raw material with D-ribose, inosine and guanosine respectively, is the synthetic 1-O-ethanoyl-2,3 of starting raw material with inosine and guanosine wherein; 5-three-O-benzoyl--β-D-ribofuranose can have the nitrogen heterocyclic ring by product to produce, and need recycle; Simultaneously, to cannot say for sure to demonstrate,prove be the β-type (acetoxyl group that is the 1-position is in the β position) of higher degree to products obtained therefrom.What adopt at present extensively is that people such as Recondon develops being starting raw material, preparing the method for title product through three-step reaction with D-ribose of formation; The synthetic title product that obtains of this method is β-type; Fusing point is 130~132 ℃, but the product yield of this method is lower, cost is higher, the organic waste quantity discharged is higher.
Summary of the invention
The technical problem that the present invention will solve is: the 1-O-ethanoyl-2,3 that a kind of product yield is higher, cost is lower, the organic waste quantity discharged is few is provided, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose.
The technical solution adopted for the present invention to solve the technical problems is: a kind of 1-O-ethanoyl-2,3, and the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose, operational path is:
Concrete steps are:
(1) glycosylation reaction drips acyl halide in methyl alcohol, generates the methanol solution of hydrogen halide, the ice-water bath cooling; Stirred 10~15 minutes, and added D-ribose then, in the time of 0~5 ℃, carried out glycosylation reaction 8 hours; Reaction finish the back with in the inorganic weak bases with system in hydrogen halide, continue to stir 30min, filtration; Concentrating under reduced pressure is removed methyl alcohol, and getting enriched material is the glucosides thing, directly is used for next step reaction;
(2) the benzoylation reaction mixes the pyridine of glucosides thing with organic solvent, catalytic amount, and heating for dissolving adds the inorganic weak bases acid binding agent then; Between 40~80 ℃, drip Benzoyl chloride 99min. and carry out the benzoylation reaction, drip back insulation 4~8 hours, suction filtration falls the insolubles in the system; Washing filtrate merges, successively after the washing of the sulphuric acid soln of water and 1.5mol/L, again with washing neutrality; Through anhydrous magnesium sulfate drying, filter then, concentrating under reduced pressure falls solvent; Get benzoylate, directly be used for next step reaction;
(3) under the acetylization reaction room temperature gained enriched material is mixed with glacial acetic acid, aceticanhydride and solubility promoter, in the time of-5~5 ℃, add a small amount of vitriol oil then,, carry out acetylization reaction in 5 ℃ of stirrings; Be incubated 5~8 hours, add frozen water and temperature control then, stirred 2~5 hours below 25 ℃; Cross and filter bullion, use ethyl alcohol recrystallization, suction filtration; Dry 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose.
Acyl halide is Acetyl Chloride 98Min., propionyl chloride, sulfur oxychloride, acetyl bromide, PROPIONYL CHLORIDE in the said step (1), preferred Acetyl Chloride 98Min. or sulfur oxychloride; The used inorganic weak bases that neutralizes is yellow soda ash, sodium hydrogencarbonate, salt of wormwood, saleratus, preferred yellow soda ash.
Organic solvent is ETHYLE ACETATE, propyl acetate, ethylene dichloride in the said step (2), ethyl acetate; The inorganic weak bases acid binding agent is yellow soda ash, sodium hydrogencarbonate, salt of wormwood, saleratus, preferred salt of wormwood; Pyridine add-on ratio: D-ribose: pyridine is 1g: 0.5ml, preferred 60~70 ℃ of temperature of reaction.
Solubility promoter is acetone, acetonitrile, THF or 1 in the said step (3), the 4-dioxane, and preferred acetone, solubility promoter usage ratio: D-ribose: solubility promoter is 1g: 1ml; The purpose that adds solubility promoter is to freeze in order to suppress glacial acetic acid and between-5~5 ℃, be incubated, and guaranteeing to react can be smoothly, steadily carry out.
Step of the present invention (1) is a starting raw material with D-ribose; Hydrogen halide is a catalyzer, adopts 0~5 ℃ low temperature glycosylation reaction, can effectively reduce the generation of pyranose ring; Pyridine or potassium hydroxide solution with adopting in the inorganic weak bases replacement document can make operation become simply, not produce the pyridine stink; The higher relatively organic solvent of boiling point is adopted in the reaction of step (2) benzoylation; Can make to be reflected at higher temperature and to carry out, be acid binding agent with the inorganic weak bases, do not use triethylamine; Only use the pyridine of catalytic amount, greatly reduce the content of nitrogenous organic waste in production cost and the waste water; Add solubility promoter in step (3) the acetylization reaction system, effectively suppressed the curing of Glacial acetic acid min. 99.5, improved the flowability of reaction system, help successful reaction and carry out.
Preparation technology of the present invention is simple to operate, cost is lower, product yield is higher, itrogenous organic substance content is lower in the waste water; Do not contain the offensive odour that produces by pyridine in the operating environment space; Effectively improve production operation personnel's Working environment, be fit to suitability for industrialized production.
Embodiment
Below in conjunction with specific embodiment the present invention is elaborated, but the present invention is not limited to following specific embodiment.
Embodiment 1
A kind of 1-O-ethanoyl-2,3, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose has following steps:
(1) glycosylation reaction dripping thionyl chloride 5ml in 100ml methyl alcohol, the ice-water bath cooling was stirred 10~15 minutes; Add D-ribose 10g, in the time of 0~5 ℃, carried out glycosylation reaction 8 hours, with in the sodium hydrogencarbonate and the hydrogenchloride in the system; Continue to stir 30min; Filter, filtrate decompression concentrates removes methyl alcohol, gets enriched material glucosides thing 11g;
(2) the benzoylation reaction mixes glucosides thing 11g with 150ml ETHYLE ACETATE, 5ml pyridine, and heating for dissolving adds salt of wormwood 30g, between 60~70 ℃, drips Benzoyl chloride 99min. 30ml and carries out the benzoylation reaction; Drip back insulation 6 hours, suction filtration falls the insolubles in the system, and washing filtrate merges; Successively after the washing of the sulphuric acid soln of water and 1.5mol/L, again with washing neutrality, then through anhydrous magnesium sulfate drying; Filter, concentrating under reduced pressure falls solvent, gets yellow syrupy shape benzoylate;
(3) under the acetylization reaction room temperature benzoylate is mixed with 100ml glacial acetic acid, 25ml aceticanhydride and 10ml acetone, in the time of-5~5 ℃, add a small amount of vitriol oil then,, carry out the acetylization reaction reaction in 5 ℃ of stirrings; Be incubated 6 hours, add frozen water 200ml and temperature control then, stirred 3 hours below 25 ℃; Cross and filter bullion, use ethyl alcohol recrystallization, suction filtration; Normal pressure dry off-white color crystallinity 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose 24.0g.
Present embodiment gained 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose is 71.4% with respect to the yield of D-ribose, purity is 98.7% (HPLC), 130~131 ℃ of fusing points, 43.3 ° of specific optical rotations (c=1, chloroform).
Embodiment 2
A kind of 1-O-ethanoyl-2,3, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose has following steps:
(1) glycosylation reaction dripping thionyl chloride 5ml in 100ml methyl alcohol, the ice-water bath cooling was stirred 10~15 minutes; Add D-ribose 10g, in the time of 0~5 ℃, carried out glycosylation reaction 8 hours, with in the sodium hydrogencarbonate and the hydrogenchloride in the system; Continue to stir 30min; Filter, filtrate decompression concentrates removes methyl alcohol, gets enriched material glucosides thing 11g;
(2) the benzoylation reaction mixes glucosides thing 11g with 150ml ETHYLE ACETATE, 5ml pyridine, and heating for dissolving adds salt of wormwood 30g, between 40~50 ℃, drips Benzoyl chloride 99min. 30ml and carries out the benzoylation reaction; Drip back insulation 8 hours, suction filtration falls the insolubles in the system, and washing filtrate merges; Successively after the washing of the sulphuric acid soln of water and 1.5mol/L, again with washing neutrality, then through anhydrous magnesium sulfate drying; Filter, concentrating under reduced pressure falls solvent, gets yellow syrupy shape benzoylate;
(3) under the acetylization reaction room temperature benzoylate is mixed with 100ml glacial acetic acid, 25ml aceticanhydride and 10ml acetone, in the time of-5~5 ℃, add a small amount of vitriol oil then,, carry out the acetylization reaction reaction in 5 ℃ of stirrings; Be incubated 6 hours, add frozen water 200ml and temperature control then, stirred 3 hours below 25 ℃; Cross and filter bullion, use ethyl alcohol recrystallization, suction filtration; Normal pressure dry off-white color crystallinity 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose 23.1g.
Present embodiment gained 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose is 68.7% with respect to the yield of D-ribose, purity is 98.5% (HPLC), 130~132 ℃ of fusing points, 43.5 ° of specific optical rotations (c=1, chloroform).
Embodiment 3
A kind of 1-O-ethanoyl-2,3, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose has following steps:
(1) glycosylation reaction dripping thionyl chloride 5ml in 100ml methyl alcohol, the ice-water bath cooling was stirred 10~15 minutes; Add D-ribose 10g, in the time of 0~5 ℃, carried out glycosylation reaction 8 hours, with in the sodium hydrogencarbonate and the hydrogenchloride in the system; Continue to stir 30min; Filter, filtrate decompression concentrates removes methyl alcohol, gets enriched material glucosides thing 11g;
(2) the benzoylation reaction mixes glucosides thing 11g with 150ml ethylene dichloride, 5ml pyridine, and heating for dissolving adds salt of wormwood 30g, between 40~50 ℃, drips Benzoyl chloride 99min. 30ml and carries out the benzoylation reaction; Drip back insulation 6 hours, suction filtration falls the insolubles in the system, and washing filtrate merges; Successively after the washing of the sulphuric acid soln of water and 1.5mol/L, again with washing neutrality, then through anhydrous magnesium sulfate drying; Filter, concentrating under reduced pressure falls solvent, gets yellow syrupy shape benzoylate;
(3) under the acetylization reaction room temperature benzoylate is mixed with 100ml glacial acetic acid, 25ml aceticanhydride and 10ml acetone, in the time of-5~5 ℃, add a small amount of vitriol oil then,, carry out the acetylization reaction reaction in 5 ℃ of stirrings; Be incubated 6 hours, add frozen water 200ml and temperature control then, stirred 3 hours below 25 ℃; Cross and filter bullion, use ethyl alcohol recrystallization, suction filtration; Normal pressure dry off-white color crystallinity 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose 22.5g.
Present embodiment gained 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose is 66.9% with respect to the yield of D-ribose, purity is 98.3% (HPLC), 130~131 ℃ of fusing points, 43.0 ° of specific optical rotations (c=1, chloroform).
Embodiment 4
A kind of 1-O-ethanoyl-2,3, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose has following steps:
(1) glycosylation reaction dripping thionyl chloride 5ml in 100ml methyl alcohol, the ice-water bath cooling was stirred 10~15 minutes; Add D-ribose 10g, in the time of 0~5 ℃, carried out glycosylation reaction 8 hours, with in the sodium hydrogencarbonate and the hydrogenchloride in the system; Continue to stir 30min; Filter, filtrate decompression concentrates removes methyl alcohol, gets enriched material glucosides thing 11g;
(2) the benzoylation reaction mixes glucosides thing 11g with 150ml ethylene dichloride, 5ml pyridine, and heating for dissolving adds salt of wormwood 30g, between 40~50 ℃, drips Benzoyl chloride 99min. 30ml and carries out the benzoylation reaction; Drip back insulation 6 hours, suction filtration falls the insolubles in the system, and washing filtrate merges; Successively after the washing of the sulphuric acid soln of water and 1.5mol/L, again with washing neutrality, then through anhydrous magnesium sulfate drying; Filter, concentrating under reduced pressure falls solvent, gets yellow syrupy shape benzoylate;
(3) under the acetylization reaction room temperature benzoylate is mixed with 100ml glacial acetic acid, 25ml aceticanhydride and 10ml acetonitrile, in the time of-5~5 ℃, add a small amount of vitriol oil then,, carry out the acetylization reaction reaction in 5 ℃ of stirrings; Be incubated 6 hours, add frozen water 200ml and temperature control then, stirred 3 hours below 25 ℃; Cross and filter bullion, use ethyl alcohol recrystallization, suction filtration; Normal pressure dry off-white color crystallinity 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose 23.6g.
Present embodiment gained 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose is 70.2% with respect to the yield of D-ribose, purity is 98.5% (HPLC), 130~132 ℃ of fusing points, 43.0 ° of specific optical rotations (c=1, chloroform).
Claims (7)
1. 1-O-ethanoyl-2,3, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose is characterized in that: have following steps:
(1) glycosylation reaction drips acyl halide in methyl alcohol, generates the methanol solution of hydrogen halide, the ice-water bath cooling; Stirred 10~15 minutes, and added D-ribose then, in the time of 0~5 ℃, carried out glycosylation reaction 8 hours; Reaction finish the back with in the inorganic weak bases with system in hydrogen halide, continue to stir 30min, filtration; Concentrating under reduced pressure is removed methyl alcohol, and getting enriched material is the glucosides thing, directly is used for next step reaction;
(2) the benzoylation reaction mixes the glucosides thing with organic solvent, pyridine, and heating for dissolving adds the inorganic weak bases acid binding agent then, between 40~80 ℃, drips Benzoyl chloride 99min. and carries out the benzoylation reaction; Drip back insulation 4~8 hours, suction filtration falls the insolubles in the system, and washing filtrate merges, successively after the washing of the sulphuric acid soln of water and 1.5mol/L; With washing neutrality,, filter again then through anhydrous magnesium sulfate drying; Concentrating under reduced pressure falls solvent, gets benzoylate, directly is used for next step reaction;
(3) under the acetylization reaction room temperature gained enriched material is mixed with glacial acetic acid, aceticanhydride and solubility promoter, in the time of-5~5 ℃, add the vitriol oil then,, carry out the acetylization reaction reaction in 5 ℃ of stirrings; Be incubated 5~8 hours, add frozen water and temperature control then, stirred 2~5 hours below 25 ℃; Cross and filter bullion, use ethyl alcohol recrystallization, suction filtration; Dry 1-O-ethanoyl-2,3,5-three-O-benzoyl--β-D-ribofuranose.
2. 1-O-ethanoyl-2,3 as claimed in claim 1, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose is characterized in that: acyl halide is Acetyl Chloride 98Min., propionyl chloride, sulfur oxychloride, acetyl bromide, PROPIONYL CHLORIDE in the said step (1); The used inorganic weak bases that neutralizes is yellow soda ash, sodium hydrogencarbonate, salt of wormwood, saleratus.
3. 1-O-ethanoyl-2,3 as claimed in claim 1, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose is characterized in that: organic solvent is ETHYLE ACETATE, propyl acetate, ethylene dichloride in the said step (2); The inorganic weak bases acid binding agent is yellow soda ash, sodium hydrogencarbonate, salt of wormwood, saleratus; Pyridine add-on ratio: D-ribose: pyridine is 1g: 0.5ml, preferred 60~70 ℃ of temperature of reaction.
4. 1-O-ethanoyl-2 as claimed in claim 1; 3; The preparation technology of 5-three-O-benzoyl--β-D-ribofuranose; It is characterized in that: solubility promoter is acetone, acetonitrile, THF or 1 in the said step (3), the 4-dioxane, and solubility promoter usage ratio: D-ribose: solubility promoter is 1g: 1ml.
5. 1-O-ethanoyl-2,3 as claimed in claim 2, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose is characterized in that: preferred Acetyl Chloride 98Min. of acyl halide or sulfur oxychloride in the said step (1), the preferred yellow soda ash of the used inorganic weak bases that neutralizes.
6. 1-O-ethanoyl-2,3 as claimed in claim 3, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose is characterized in that: organic solvent ethyl acetate in the said step (2), the preferred salt of wormwood of inorganic weak bases acid binding agent.
7. 1-O-ethanoyl-2,3 as claimed in claim 4, the preparation technology of 5-three-O-benzoyl--β-D-ribofuranose is characterized in that: the preferred acetone of solubility promoter in the said step (3).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2012101045585A CN102659856A (en) | 2012-04-10 | 2012-04-10 | Preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2012101045585A CN102659856A (en) | 2012-04-10 | 2012-04-10 | Preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose |
Publications (1)
Publication Number | Publication Date |
---|---|
CN102659856A true CN102659856A (en) | 2012-09-12 |
Family
ID=46769464
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2012101045585A Pending CN102659856A (en) | 2012-04-10 | 2012-04-10 | Preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102659856A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103641801A (en) * | 2013-11-14 | 2014-03-19 | 博通维德(北京)生物科技有限公司 | Stearic acid-tetrahydrofuran-3,4-diester synthetic method |
CN108314696A (en) * | 2018-03-16 | 2018-07-24 | 上药康丽(常州)药业有限公司 | 2- hydroxyls -1,3, the utilization method of tri--O- benzoyls-α of 5--D-RIBOSE crystalline mother solution |
CN108570078A (en) * | 2018-07-18 | 2018-09-25 | 荆门医药工业技术研究院 | A method of preparing three-O- benzoyls-β of 1-O- acetyl group -2,3,5--D-RIBOSE |
CN111484535A (en) * | 2020-03-31 | 2020-08-04 | 和德化学(苏州)有限公司 | Method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4924977A (en) * | 1972-06-30 | 1974-03-05 | ||
EP0072977A1 (en) * | 1981-08-19 | 1983-03-02 | Starks Associates, Incorporated | Process for the production of 2-beta-D-ribofuranosylthiazole-4-carboxamide |
JPH0924977A (en) * | 1995-07-11 | 1997-01-28 | Wing:Kk | Bag for vacuum-packaging fish, meat or the like |
CN1747961A (en) * | 2003-02-10 | 2006-03-15 | 英娜尔科公司 | Process for the preparation of ribofuranose derivatives |
CN101274950A (en) * | 2008-03-31 | 2008-10-01 | 葛建利 | Production process for preparing 1-oxy-acetyl-2,3,5-3-benzoyl-beta-Lribofuranose |
WO2010150791A1 (en) * | 2009-06-23 | 2010-12-29 | ヤマサ醤油株式会社 | Process for production of adenosine tetraphosphate compound |
CN102000103A (en) * | 2009-12-21 | 2011-04-06 | 郑州大学 | Medicinal application of 2'-fluoro-4'-nitrine-nucleoside analogues or salt thereof |
-
2012
- 2012-04-10 CN CN2012101045585A patent/CN102659856A/en active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4924977A (en) * | 1972-06-30 | 1974-03-05 | ||
EP0072977A1 (en) * | 1981-08-19 | 1983-03-02 | Starks Associates, Incorporated | Process for the production of 2-beta-D-ribofuranosylthiazole-4-carboxamide |
JPH0924977A (en) * | 1995-07-11 | 1997-01-28 | Wing:Kk | Bag for vacuum-packaging fish, meat or the like |
CN1747961A (en) * | 2003-02-10 | 2006-03-15 | 英娜尔科公司 | Process for the preparation of ribofuranose derivatives |
CN101274950A (en) * | 2008-03-31 | 2008-10-01 | 葛建利 | Production process for preparing 1-oxy-acetyl-2,3,5-3-benzoyl-beta-Lribofuranose |
WO2010150791A1 (en) * | 2009-06-23 | 2010-12-29 | ヤマサ醤油株式会社 | Process for production of adenosine tetraphosphate compound |
CN102000103A (en) * | 2009-12-21 | 2011-04-06 | 郑州大学 | Medicinal application of 2'-fluoro-4'-nitrine-nucleoside analogues or salt thereof |
Non-Patent Citations (2)
Title |
---|
《精细化工中间体》 20091031 邓燕,等 1-乙酰氧基-2,3,5-三-苯甲酰氧基-beta-D-呋喃核糖的合成工艺改进 30-33 1-7 第39卷, 第5期 * |
邓燕,等: "1-乙酰氧基-2,3,5-三-苯甲酰氧基-β-D-呋喃核糖的合成工艺改进", 《精细化工中间体》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103641801A (en) * | 2013-11-14 | 2014-03-19 | 博通维德(北京)生物科技有限公司 | Stearic acid-tetrahydrofuran-3,4-diester synthetic method |
CN108314696A (en) * | 2018-03-16 | 2018-07-24 | 上药康丽(常州)药业有限公司 | 2- hydroxyls -1,3, the utilization method of tri--O- benzoyls-α of 5--D-RIBOSE crystalline mother solution |
CN108314696B (en) * | 2018-03-16 | 2021-07-13 | 上药康丽(常州)药业有限公司 | Utilization method of 2-hydroxy-1, 3, 5-tri-O-benzoyl-alpha-D-ribofuranose crystallization mother liquor |
CN108570078A (en) * | 2018-07-18 | 2018-09-25 | 荆门医药工业技术研究院 | A method of preparing three-O- benzoyls-β of 1-O- acetyl group -2,3,5--D-RIBOSE |
CN111484535A (en) * | 2020-03-31 | 2020-08-04 | 和德化学(苏州)有限公司 | Method for preparing 1-O-acetyl-2, 3, 5-tri-O-benzoyl-1- β -D-ribofuranose |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102659856A (en) | Preparation technology of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose | |
CN101497639A (en) | Preparation of decitabine | |
CN102212095A (en) | Preparation methods of capecitabine and intermediate thereof | |
CN101302207B (en) | Preparation of 3-o-alkyl-5,6-o-(1-methyl ethylidine)-l-ascorbic acid and preparation of 5,6-o-(1- methyl ethylidine)-l- ascorbic acid | |
CN102153601A (en) | Method for preparing gemcitabine hydrochloride and intermediate thereof with high selectivity | |
SK283649B6 (en) | Novel method for isomerising the 10-methyl radical of erythromycin derivatives | |
CN104109157B (en) | The preparation method that Ka Gelie is clean | |
CN103130855B (en) | Preparation method of decitabine | |
CN103288890B (en) | One prepares 3-O-benzyl-1, the new method of 2-O-isopropylidene-β-L-furan idose | |
CN103709209A (en) | Isopropyl-beta-D-thiogalactoside preparation method | |
AU756816B2 (en) | Glycosidation of 4,5-epoxymorphinan-6-ols | |
CN108440623A (en) | A kind of preparation method and products thereof of capecitabine intermediate | |
CN104650160A (en) | Novel synthesis method of capecitabine key intermediate 1,2,3-O-triacetyl-5-deoxy-D-ribose | |
CN104513137B (en) | A kind of 1,5-eneyne alcohol compound and synthetic method and application | |
CN104109182A (en) | Preparation method of gemcitabine hydrochloride | |
JP2003532736A (en) | Uridine derivatives as antibiotics | |
CN1159331C (en) | Prepn. of 2',3'-didehydro-3'-deoxythymidine | |
ITMI971211A1 (en) | PRODUCTION FOR THE PREPARATION OF A DESOXYURIDINE DERIVATIVE | |
CN105985346B (en) | A kind of new ticagrelor compounds process for production thereof and its midbody compound | |
CN100513391C (en) | Process for full water phase synthesis of pharmaceutical intermediate dimethyl cyanoiminodithio-carbonate | |
CN103709210A (en) | Isopropyl-beta-D-thiogalactoside preparation technology | |
Shimomura et al. | Stereoselective Syntheses of. BETA.-D-Ribonucleosides Catalyzed by the Combined Use of Silver Salts and Diphenyltin Sulfide or Lawesson's Reagent. | |
KR100446560B1 (en) | Method for Producing 2-Deoxy-L-ribose | |
CN101805350A (en) | Synthesis method of imperatorin derivative | |
CN102424697A (en) | 2',3'- di-O-acetyl-5'-deoxy-5-fulurocytidineonium compound and preparation method thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120912 |