CN103739635A - Method for purifying 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate - Google Patents
Method for purifying 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate Download PDFInfo
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Abstract
The invention provides a method for purifying a 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate. The method comprises the following steps: adding a crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product into mixed liquid containing n-butyl alcohol and 2-methoxyethanol; heating the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product until the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product is dissolved; cooling the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product until the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product is completely crystallized; performing filtering, washing and drying to obtain the 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate, namely a 1,3,4,6-tetraacetyl-beta-D-mannopyranose crystal. The yield and purity of the 1,3,4,6-tetraacetyl-beta-D-mannopyranose are remarkably improved, so that the problems of low yield and low purity of the synthesized 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate namely 1,3,4,6-tetraacetyl-beta-D-mannopyranose in the prior art are solved.
Description
Technical field
The invention belongs to separation and purification field, be specifically related to a kind of mannose triflate intermediate, 1,3,4,6-is tetra-acetylated-purification process of β-D-MANNOSE.
Background technology
The chemical name of mannose triflate is 1,3,4,6-, tetra--O-ethanoyl-2-O-trifyl-β-D-MANNOSE, is synthetic PET developer
18the precursor of F-FDG.At present,
18f-FDG is most popular tracer agent in positron emission fault (PET) video picture, not only be widely used in laboratory study, but also be widely used in the daily clinical diagnosis of cardiovascular, nerve and tumour etc., it uses and has accounted for the more than 90% of PET video picture clinical application, thereby the demand of mannose triflate is increased, thereby the productive rate to mannose triflate synthetic in prior art and purity need to propose higher requirement to meet the great demand amount of mannose triflate.
At present, the industrial production of mannose triflate relates to multistep chemosynthesis, optimize each synthesis step most important for the reduction of cost and the productive rate of mannose triflate and purity, the yield of raising intermediate and purity can make the productive rate of final product mannose triflate, purity all improves greatly, and yield and the purity of raising reaction intermediate, particularly in reaction intermediate yield and the purity of post-synthesis phase, for providing, to meet the quality control specification standards of for example mannose triflate described in European Pharmacopoeia extremely important, the final medicine meeting described in American Pharmacopeia for example providing is be provided simultaneously
18f-FDG (2-
18f-2-DDG) quality control specification standards also extremely important.
But mannose triflate is synthesizing in the prior art; greatly mainly with 1; 3; 4; 6-is tetra-acetylated-and β-D-MANNOSE is the building-up reactions that intermediate carries out the later stage, therefore 1,3; 4,6-is tetra-acetylated-and yield and the purity of β-D-MANNOSE is even more important for the productive rate of product mannose triflate, the impact of purity.
The synthetic method of disclosed mannose triflate in prior art, as Russ P document RU2165266C1, the paper < < PracticalandReliableSynthesisof 1 that the people such as the synthetic > > of the < < diagnostic reagent mannose triflate that Yang Zhijie delivers and Tatsushi Toyokuni deliver, 3, 4, 6-Tetra-O-acetyl-2-Otrifluoromethanesulfonyl-β-D-mannopyra nose, aPrecursorof2-Deoxy-2-[
18f] fluoro-D-glucose (FDG) > >, wherein the synthetic method of disclosed mannose triflate mainly contains three kinds, these three kinds of methods are by reaction intermediate 1, 3, 4, 6-is tetra-acetylated-and β-D-MANNOSE (1) makes with equimolar trifluoromethanesulfonic acid anhydride reactant, and reaction equation is as follows:
For above-mentioned intermediate-1; 3; 4; 6-is tetra-acetylated-β-D-MANNOSE synthetic; the paper < < PracticalandReliableSynthesisof 1,3,4 that the people such as Tatsushi Toyokuni delivered in 2004; 6-Tetra-O-acetyl-2-Otrifluoromethanesulfonyl-β-D-mannopyra nose, aPrecursorof2-Deoxy-2-[
18f] in fluoro-D-glucose (FDG) > >; disclose 1; 3; 4; 6-is tetra-acetylated-and β-D-MANNOSE (1) is take D-MANNOSE as raw material; through acetylize, bromo, cyclization, then generate with hydrochloric acid hydrolysis, reaction equation is as follows:
The hydrolysis reaction of the 4th step in above-mentioned steps can produce two major impurities 2,3,4,6-is tetra-acetylated-β-D-MANNOSE (4) and 2,3,4,6-tetra-acetylated-α-D-MANNOSE (5) (See Figure formula).Wherein, 2,3; 4; 6-is tetra-acetylated-and the unstable meeting of α-D-MANNOSE (5) is converted into 2,3,4 very soon; 6-is tetra-acetylated-β-D-MANNOSE (4); in addition, 1,3; 4,6-is tetra-acetylated-and β-D-MANNOSE (1) can shift and be gradually transformed into impurity (4) and (5) by acyl group.
Although in above-mentioned document, disclose 1,3,4,6-tetra-acetylated-β-D-MANNOSE (1) can pass through ethyl alcohol recrystallization, its recrystallization yield is lower, only has less than 50%.For another example in Chinese patent literature CN1911947A and CN101659682A, all disclose 1; 3,4,6-is tetra-acetylated-synthesis step of β-D-MANNOSE (1); both adopt to add ether crystallization and then obtain 1 of certain yield and purity; 3,4,6-is tetra-acetylated-β-D-MANNOSE (1); but 1 of its acquisition; 3,4,6-is tetra-acetylated-and yield and the purity of β-D-MANNOSE is not high yet.
Summary of the invention
For this reason; technical problem to be solved by this invention is mannose triflate intermediate 1 synthetic in prior art; 3; 4; 6-is tetra-acetylated-yield of β-D-MANNOSE and purity not high and then affect the productive rate of synthetic mannose triflate and the problem of purity, and then provide one can significantly improve 1,3; 4,6-is tetra-acetylated-yield of β-D-MANNOSE and the purification process of purity.
For solving the problems of the technologies described above, the invention provides a kind of 1,3,4,6-tetra-acetylated-purification process of β-D-MANNOSE, comprise the steps,
Get synthetic obtain 1,3,4; 6-is tetra-acetylated-and β-D-MANNOSE crude product is added in the mixing liquid containing propyl carbinol and ethylene glycol monomethyl ether; be heated to dissolve, and it is complete to be cooled to subsequently crystallization, filters; washing; dry, obtain mannose triflate intermediate 1,3; 4,6-is tetra-acetylated-β-D-MANNOSE crystal.
In the purification process of above-mentioned mannose triflate intermediate, the volume ratio of described propyl carbinol and described ethylene glycol monomethyl ether is 4-8:1.
In the purification process of above-mentioned mannose triflate intermediate, the volume ratio of described propyl carbinol and described ethylene glycol monomethyl ether is 6:1.
In the purification process of above-mentioned mannose triflate intermediate, described 1,3,4,6-is tetra-acetylated-and the weight of β-D-MANNOSE crude product and the volume ratio of the described mixing liquid containing propyl carbinol and ethylene glycol monomethyl ether are 1:5-15; The relation that described weight and the proportionlity of volume are g/mL.
In the purification process of above-mentioned mannose triflate intermediate, described 1,3,4,6-is tetra-acetylated-and the weight of β-D-MANNOSE crude product and the volume ratio of the described mixing liquid containing propyl carbinol and ethylene glycol monomethyl ether are 1:10.
In the purification process of above-mentioned mannose triflate intermediate, in the step of described decrease temperature crystalline, contain described in control 1,3,4,6-tetra-acetylated-lysate of β-D-MANNOSE is cooled to 8-15 ℃, is preferably cooled to 10 ℃.
In the purification process of above-mentioned mannose triflate intermediate, in the crystal step that described washing leaches, to account for butanol solution repeated washing 2-3 time that the crystal weight 0.3-0.8 volume that leaches doubly measures, preferably to account for butanol solution repeated washing 2-3 time that crystal weight 0.5 volume that leaches doubly measures; The pass that the weight of described crystal and the volume of described butanol solution are doubly measured is the relation of g/ml.
In the purification process of above-mentioned mannose triflate intermediate, in described drying step, control crystal after described washing in 45-55 ℃, vacuum-drying 8-12 hour, preferably control crystal after described washing in 50 ℃, vacuum-drying 10 hours.
The present invention by above-mentioned purification process make 1,3,4,6-tetra-acetylated-β-D-MANNOSE.
The purification process of mannose triflate intermediate of the present invention is being prepared the application in mannose triflate and synthetic PET developer field.
Technique scheme of the present invention has the following advantages compared to existing technology:
(1) purification process of mannose triflate intermediate of the present invention, utilize the pure solution of propyl carbinol and ethylene glycol monomethyl ether to be mixed to get mixing liquid, as recrystallisation solvent to mannose triflate intermediate 1, 3, 4, 6-is tetra-acetylated-and β-D-MANNOSE carries out purification, improved significantly 1, 3, 4, 6-is tetra-acetylated-yield and the purity of β-D-MANNOSE, average yield reaches 75.8%, purity is up to 99.5%, with respect to the yield of 40% left and right in prior art, there is significant raising, thereby solved synthetic mannose triflate intermediate 1 in prior art, 3, 4, 6-is tetra-acetylated-yield and the not high problem of purity of β-D-MANNOSE, by method of the present invention, obtain simultaneously 1, 3, 4, 6-is tetra-acetylated-and β-D-MANNOSE also has good stability, the advantage of long quality-guarantee period,
(2) purification process of mannose triflate intermediate of the present invention, by controlling in mixing liquid, the volume ratio of described propyl carbinol and ethylene glycol monomethyl ether is 4-8:1, significantly improved 1,3,4,6-tetra-acetylated-yield and the purity of β-D-MANNOSE;
(3) purification process of mannose triflate intermediate of the present invention, by controlling 1,3,4,6-is tetra-acetylated-and the ratio of the weight of β-D-MANNOSE crude product and the volume of described propyl carbinol and ethylene glycol monomethyl ether mixing solutions is 1:5-15, has significantly improved 1,3,4,6-is tetra-acetylated-yield and the purity of β-D-MANNOSE;
(4) purification process of mannose triflate intermediate of the present invention can be widely used in preparing mannose triflate and PET developer
18the fields such as F-FDG.
Embodiment
In following embodiment for the elaboration of the technique effect of purification process of the present invention; as an example of disclosed method in prior art example, carry out 1; 3; 4,6-is tetra-acetylated-preparation of β-D-MANNOSE, select according to published reference < < PracticalandReliableSynthesisof 1; 3; 4,6-Tetra-O-acetyl-2-Otrifluoromethanesulfonyl-β-D-mannopyra nose, aPrecursorof2-Deoxy-2-[
18f] the described synthetic method recorded in fluoro-D-glucose (FDG) > > is example; take triacetyl dioxa glutinous rehmannia seminose as raw material; obtain 1 of processing to be purified; 3; 4; 6-is tetra-acetylated-β-D-MANNOSE crude product: and the triacetyl dioxa glutinous rehmannia seminose (3) of 56g is dissolved in the acetone of 140mL, adds the HCl solution of the 1M of 33.6mL, bath temperature is controlled at 18 ℃ of left and right.After room temperature reaction 10 minutes, evaporate to dryness obtains white solid.Add the CHCl of 120mL
3dissolve this solid, then use the distilled water wash three times of 60mL.Through anhydrous sodium sulfate drying, filter.Filtrate, through evaporate to dryness, obtains yellow oil.Add the ether of 60mL fully to stir, separate out white solid, suction filtration, vacuum-drying, obtain 1,3,4,6-tetra-acetylated-β-D-MANNOSE crude product 14g, the foreign matter content detecting in described crude product is 0.678g, mp:159-163 ℃.
Embodiment 1
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, comprise the steps:
In there-necked flask, add the described mixing liquid 50mL containing propyl carbinol and ethylene glycol monomethyl ether, the ratio of described propyl carbinol and ethylene glycol monomethyl ether volume is 6:1, add above-mentioned make 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crude product 10g, and solution is heated to 80 ℃, until 1, 3, 4, 6-is tetra-acetylated-and β-D-MANNOSE crude product dissolves completely, subsequently above-mentioned lysate is cooled to 8 ℃, and standing crystallization 1 hour, filter the solution of above-mentioned crystallization, add the above-mentioned crystal leaching of 3mL butanol solution washing, repeated washing 2-3 time, by washing after crystal in 45 ℃ of vacuum-dryings 8 hours, obtain 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crystal.
Embodiment 2
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, comprise the steps:
In there-necked flask, add the described mixing liquid 100mL containing propyl carbinol and ethylene glycol monomethyl ether, the ratio of described propyl carbinol and ethylene glycol monomethyl ether volume is 6:1, add above-mentioned make 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crude product 10g, and solution is heated to 100 ℃, until described 1, 3, 4, 6-is tetra-acetylated-and β-D-MANNOSE crude product dissolves completely, subsequently above-mentioned lysate is cooled to 10 ℃, and standing crystallization 2 hours, filter the solution of above-mentioned crystallization, add the above-mentioned crystal leaching of 5mL butanol solution washing, repeated washing 2-3 time, by washing after crystal in 50 ℃ of vacuum-dryings 10 hours, obtain described 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crystal.
Embodiment 3
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, comprise the steps:
In there-necked flask, add the described mixing liquid 150mL containing propyl carbinol and ethylene glycol monomethyl ether, the ratio of described propyl carbinol and ethylene glycol monomethyl ether volume is 6:1, add above-mentioned make 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crude product 10g, and solution is heated to 110 ℃, until described 1, 3, 4, 6-is tetra-acetylated-and β-D-MANNOSE crude product dissolves completely, subsequently above-mentioned lysate is cooled to 15 ℃, and standing crystallization 3 hours, filter the solution of above-mentioned crystallization, add the above-mentioned crystal leaching of 7mL butanol solution washing, repeated washing 2-3 time, by washing after crystal in 55 ℃ of vacuum-dryings 12 hours, obtain described 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crystal.
Embodiment 4
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, comprise the steps:
In there-necked flask, add the described mixing liquid 100mL containing propyl carbinol and ethylene glycol monomethyl ether, the ratio of described propyl carbinol and ethylene glycol monomethyl ether volume is 4:1, add above-mentioned make 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crude product 10g, and solution is heated to 100 ℃, until described 1, 3, 4, 6-is tetra-acetylated-and β-D-MANNOSE crude product dissolves completely, subsequently above-mentioned lysate is cooled to 10 ℃, and standing crystallization 2 hours, filter the solution of above-mentioned crystallization, add the above-mentioned crystal leaching of 5mL butanol solution washing, repeated washing 2-3 time, by washing after crystal in 50 ℃ of vacuum-dryings 10 hours, obtain described 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crystal.
Embodiment 5
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, comprise the steps:
In there-necked flask, add the described mixing liquid 50mL containing propyl carbinol and ethylene glycol monomethyl ether, the ratio of described propyl carbinol and ethylene glycol monomethyl ether volume is 8:1, add above-mentioned make 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crude product 10g, and solution is heated to 100 ℃, until described 1, 3, 4, 6-is tetra-acetylated-and β-D-MANNOSE crude product dissolves completely, subsequently above-mentioned lysate is cooled to 10 ℃, and standing crystallization 2 hours, filter the solution of above-mentioned crystallization, add the above-mentioned crystal leaching of 5mL butanol solution washing, repeated washing 2-3 time, by washing after crystal in 50 ℃ of vacuum-dryings 10 hours, obtain described 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crystal.
Comparative example 1
Described 1,3,4 of the present embodiment; 6-is tetra-acetylated-purification process of β-D-MANNOSE and the purification step of above-described embodiment 3 basic identical, difference is only that the recrystallisation solvent adopting in the present embodiment is ethanol, obtains described 1; 3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
Comparative example 2
Described 1,3,4 of the present embodiment; 6-is tetra-acetylated-purification process of β-D-MANNOSE and the purification step of above-described embodiment 3 basic identical, difference is only that the recrystallisation solvent adopting in the present embodiment is ether, obtains described 1; 3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
Comparative example 3
Described 1,3,4 of the present embodiment; 6-is tetra-acetylated-purification process of β-D-MANNOSE and the purification step of above-described embodiment 3 basic identical, difference is only that the recrystallisation solvent adopting in the present embodiment is propyl carbinol, obtains described 1; 3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
Comparative example 4
Described 1,3,4 of the present embodiment; 6-is tetra-acetylated-purification process of β-D-MANNOSE and the purification step of above-described embodiment 3 basic identical, difference is only that the recrystallisation solvent adopting in the present embodiment is ethylene glycol monomethyl ether, obtains described 1; 3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
Effect example
To use in above-described embodiment 1,3,4; 6-is tetra-acetylated-through crystallization purifying, obtain in β-D-MANNOSE crude product and embodiment 1-3, comparative example 1-4 1,3,4; 6-is tetra-acetylated-and β-D-MANNOSE carries out HPLC analysis, and described HPLC analysis condition is as follows: analysis mode chromatographic column: C
18reverse-phase chromatographic column, particle diameter is 5um, pillar specification is 250*4.6mm; mobile phase composition volume ratio is acetonitrile: water=65:35; operating temperature is 25 ℃, and flow velocity is for being 1.0L/min, and detection wavelength is 220nm; appearance time is 3.3min; detect described 1,3,4; 6-is tetra-acetylated-purity of β-D-MANNOSE and the content of impurity, and the purity outcome record obtaining is in following table.
According to formula 1,3,4; 6-is tetra-acetylated-β-D-MANNOSE crystal yield/1, and 3,4; 6-is tetra-acetylated-and the amount * 100% of β-D-MANNOSE crude product, calculates described in each embodiment and comparative example 1,3; 4,6-is tetra-acetylated-yield of β-D-MANNOSE, and wherein said 1; 3; 4,6-is tetra-acetylated-and the amount of β-D-MANNOSE crude product is 10g, and the yield outcome record obtaining is in following table.
The effect data of the each embodiment of table 1
By the above results, relatively found, purification process of the present invention obtain 1,3; 4,6-is tetra-acetylated-and the yield of β-D-MANNOSE on average reaches 75.8%, and purity on average reaches 99.5%; show thus, purification process of the present invention has improved 1,3 significantly; 4; 6-is tetra-acetylated-yield and the purity of β-D-MANNOSE, thus solved synthetic mannose triflate intermediate 1,3 in prior art; 4,6-is tetra-acetylated-yield and the not high problem of purity of β-D-MANNOSE.
Obviously above-described embodiment is only for example is clearly described, and the not restriction to embodiment.For those of ordinary skill in the field, can also make other changes in different forms on the basis of the above description.Here without also giving exhaustive to all embodiments.And the apparent variation of being extended out thus or variation are still among the protection domain in the invention.
Claims (10)
1. a purification process for mannose triflate intermediate, is characterized in that, comprises the steps:
Get 1,3,4,6-tetra-acetylated-β-D-MANNOSE crude product is added in the mixing liquid containing propyl carbinol and ethylene glycol monomethyl ether, be heated to dissolve; and it is complete to be cooled to subsequently crystallization, filter, washing, dry; obtaining mannose triflate intermediate-1,3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
2. the purification process of mannose triflate intermediate according to claim 1, is characterized in that, the volume ratio of described propyl carbinol and described ethylene glycol monomethyl ether is 4-8:1.
3. the purification process of mannose triflate intermediate according to claim 1 and 2, is characterized in that, the volume ratio of described propyl carbinol and described ethylene glycol monomethyl ether is 6:1.
4. according to the purification process of the arbitrary described mannose triflate intermediate of claim 1-3, it is characterized in that described 1,3,4,6-is tetra-acetylated-and the weight of β-D-MANNOSE crude product and the volume ratio of the described mixing liquid containing propyl carbinol and ethylene glycol monomethyl ether are 1:5-15; The proportionlity of described weight and volume is the relation of g/mL.
5. the purification process of mannose triflate intermediate according to claim 4, is characterized in that, described 1,3,4, and 6-is tetra-acetylated-and the weight of β-D-MANNOSE crude product and the volume ratio of the described mixing liquid containing propyl carbinol and ethylene glycol monomethyl ether are 1:10.
6. according to the purification process of the arbitrary described mannose triflate intermediate of claim 1-5, it is characterized in that, in the step of described decrease temperature crystalline, contain described in control 1,3,4,6-tetra-acetylated-lysate of β-D-MANNOSE is cooled to 8-15 ℃.
7. according to the purification process of the arbitrary described mannose triflate intermediate of claim 1-6, it is characterized in that, in the crystal step that described washing leaches, to account for butanol solution repeated washing 2-3 time that the 0.3-0.8 volume of the described crystal weight leaching doubly measures; The pass that the weight of described crystal and the volume of described butanol solution are doubly measured is the relation of g/mL.
8. according to the purification process of the arbitrary described mannose triflate intermediate of claim 1-7, it is characterized in that, in described drying step, control crystal after described washing in 45-55 ℃, vacuum-drying 8-12 hour.
9. according to the arbitrary described purification process of claim 1-8, obtain 1,3,4,6-is tetra-acetylated-β-D-MANNOSE.
According to the purification process of the arbitrary described mannose triflate intermediate of claim 1-8 in the application of preparing mannose triflate and synthetic PET developer field.
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| CN104558062A (en) * | 2015-01-13 | 2015-04-29 | 天津大学 | Method for recycling byproduct associated during preparation process of mannose triflate intermediate 1,3,4,6-tetraacetyl-beta-D-mannose |
| CN106866752A (en) * | 2017-02-16 | 2017-06-20 | 内蒙古昶辉生物科技股份有限公司 | A kind of preparation method of mannose triflate |
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| CN104558062A (en) * | 2015-01-13 | 2015-04-29 | 天津大学 | Method for recycling byproduct associated during preparation process of mannose triflate intermediate 1,3,4,6-tetraacetyl-beta-D-mannose |
| CN106866752A (en) * | 2017-02-16 | 2017-06-20 | 内蒙古昶辉生物科技股份有限公司 | A kind of preparation method of mannose triflate |
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