CN102070492A - Method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde - Google Patents
Method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde Download PDFInfo
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- CN102070492A CN102070492A CN2010105930013A CN201010593001A CN102070492A CN 102070492 A CN102070492 A CN 102070492A CN 2010105930013 A CN2010105930013 A CN 2010105930013A CN 201010593001 A CN201010593001 A CN 201010593001A CN 102070492 A CN102070492 A CN 102070492A
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Abstract
The invention discloses a method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde, which uses widely available raw materials, makes operation easy, has high yield and produces little pollution. The method comprises the following process steps: dissolving 3-formoxyl-1,1'-binaphthol serving as a raw material in methanol, cooling in an ice bath, adding sodium borohydride, and reducing to obtain 3-hydroxymethyl-1,1'-binaphthol; dissolving 3-hydroxymethyl-1,1'-binaphthol in acetone serving as a solvent, adding 2,2'-dimethoxypropane to perform a reaction in the presence of a catalyst, extracting with an organic solvent, and obtaining (S)-2-hydroxy-1-(2,2-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)-naphthalene by column chromatograpic separation; dissolving (S)-2-hydroxy-1-(2,2-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)-naphthalene in dry dimethyl formamide (DMF) serving as a solvent, adding sodium hydride under an ice bath condition, reacting for 0.5 and 1 hours, adding 3-(4-methoxyphenyl)-ureido-benzyl bromide, reacting and obtaining (S)-2-(3-phenylureidobenzoxy)-1-(2,2-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)- naphthalene by column chromatograpic separation; dissolving the (S)-2-(3-phenylureidobenzoxy)-1-(2,2-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroanthracene-9-)- naphthalene in glycol serving as a solvent, heating to remove a protective group under the action of p-toluenesulfonic acid and reacting to obtain (S)-2-hydroxy-3-hydroxymethyl-2'-(3-tetrahydroanthracene)-1,1'-binaphthyl; and finally, oxidizing the (S)-2-hydroxy-3-hydroxymethyl-2'-(3-tetrahydroanthracene)-1,1'-binaphthyl in dry dichloromethane by pyridinium chlorochromate, and after reaction, filtering the reaction product by kieselguhr, concentrating and performing column chromatograpic separation to obtain the target product.
Description
Technical field
The present invention relates to a kind of with 2,2'-dimethoxy methyl-3-formyl radical-dinaphthalene be raw material synthetic (
S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1, the method for 1'-dinaphthalene-3-formaldehyde.
Background technology
Recent research shows, some binaphthol derivatives based on urea groups can be used as manual simulation's enzyme of pyridoxal phosphate, come 1 by reversible reaction with chiral amino alcohol generation schiff bases, the 2-amino alcohol carries out mapping selection identification and extraction splits, and L-amino acid is carried out the extraction fractionation of configuration conversion and DL-Amino Acid.Usually the reliable fermentation method of L-amino acid obtains, and D-amino acid still can't pass through fermentative Production at present.D-amino acid is the key intermediate of chiral drug, chirality agricultural chemicals, chirality foodstuff additive, has a wide range of applications at medicine, agricultural chemicals and field of food.Adopt (
S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1,1'-dinaphthalene-3-formaldehyde (
1) the L-amino acid that is easy to obtain can be changed into cost an arm and a leg, broad-spectrum D-amino acid.
The method of the existing synthetic both at home and abroad binaphthol derivative based on urea groups has following two kinds:
Method 1:
Method 2:
The regioselectivity of reaction is bad in the method 1, and yield is also very low.Intermediate 2'-methoxyl methyl in the method 2-3-formyl radical-dinaphthalene preparation process complicated operation, wayward, and also yield is bad, is not suitable for industrialized production.
Summary of the invention
[0004] the technical problem to be solved in the present invention provides a kind of raw material and is easy to get, the yield height, be fit to scale operation synthetic (
S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1, the method for 1'-dinaphthalene-3-formaldehyde.
Technical solution of the present invention is: with 3-formyl radical-1, the 1'-binaphthol (
2) be raw material, it is dissolved in methyl alcohol, ice bath is cooled to 0-10 ℃ and adds sodium borohydride, 3-formyl radical-1,1'-binaphthol (2) is 1.0:1.0 ~ 2.0 with the mol ratio of sodium borohydride, carries out reduction reaction under the room temperature and obtains 3-methylol-1, the 1'-binaphthol (
3); With acetone be then solvent in the presence of catalyzer, described catalyzer and 3-methylol-1, the 1'-binaphthol (
3) mol ratio 0.01:1-0.05:1 and catalyzer be a kind of among the vitriol oil, tosic acid and the PPTS, add 2, the 2'-Propanal dimethyl acetal, 3-methylol-1, the 1'-binaphthol (
3) with 2, the mol ratio of 2'-Propanal dimethyl acetal is 1.0:2.0 ~ 4.0, reaction back organic solvent extraction is concentrated under the room temperature, column chromatography for separation obtain product (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4); Be solvent to do DMF then, ice bath adds sodium hydride down, react to add 3-(4-p-methoxy-phenyl)-urea groups-bromotoluene after 0.5～1 hour, (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4): the mol ratio of sodium hydride: 3-(4-methoxyl group-phenyl)-urea groups-bromotoluene is 1.0:1.2:1.1 ~ 1.5, room temperature reaction after column chromatography for separation obtain compound (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5); Be solvent with ethylene glycol again, under the tosic acid effect, be heated to 50-70 ℃ and take off protecting group, (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5) with the mol ratio of tosic acid be 1:1.0 ~ 1:1.2, under the room temperature reaction obtain (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6); At last in the exsiccant methylene dichloride, through the pyridinium chlorochromate oxidation, (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6) with the mol ratio of pyridinium chlorochromate be 1:2.0 ~ 3.0, react under the room temperature, each step reaction is followed the tracks of reaction process with thin layer plate, then through diatomite filtration, concentrates, column chromatography for separation obtains target product, reaction formula is as follows:
Above-mentioned synthesizing (
S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1, the method for 1'-dinaphthalene-3-formaldehyde, synthetic (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4) in the process with organic solvent extraction, when concentrating, described organic solvent is ethyl acetate or methylene dichloride or chloroform.
Above-mentioned synthesizing (
S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1, the method for 1'-dinaphthalene-3-formaldehyde, synthetic (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4) to add catalyzer be the vitriol oil for time institute.
Above-mentioned synthesizing (
S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1, the method for 1'-dinaphthalene-3-formaldehyde, described organic solvent is an ethyl acetate.
Advantage of the present invention is: raw materials used source is abundant, obtain easily, and per step synthetic reaction process is simple to operate, easily row and yield are high, good reaction selectivity, avoided the generation of complicated by product, the separation purification process of per step product is simple, pollutes and lacks, and is applicable to fairly large industrial production.
Embodiment
Embodiment 1:
With 3-formyl radical-1, the 1'-binaphthol (
2) be raw material, it is dissolved in a certain amount of methyl alcohol, ice bath is cooled to 10 ℃ and adds sodium borohydride, 3-formyl radical-1, the mol ratio of 1'-binaphthol and sodium borohydride is 1.0:1.0, carries out reduction reaction under the room temperature and obtains 3-methylol-1, the 1'-binaphthol (
3); With acetone be then solvent under catalyzer (vitriol oil) condition, the described vitriol oil and 3-methylol-1, the 1'-binaphthol (
3) mol ratio is 0.01:1, adds 2, the 2'-Propanal dimethyl acetal, 3-methylol-1, the 1'-binaphthol (
3) with 2, the mol ratio of 2'-Propanal dimethyl acetal is 1.0:2.0, room temperature reaction finishes the back with organic solvent (ethyl acetate) extraction, concentrate, column chromatography for separation obtain product (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4), productive rate is 85%; Be solvent to do DMF then, ice bath adds sodium hydride down, react to add 3-(4-p-methoxy-phenyl)-urea groups-bromotoluene after one hour, (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4): the mol ratio of sodium hydride: 3-(4-methoxyl group-phenyl)-urea groups-bromotoluene is 1.0:1.2:1.2, room temperature reaction after column chromatography for separation obtain compound (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5), productive rate is 91%; Be solvent with ethylene glycol again, under the tosic acid effect, be heated to 70 ℃ and take off protecting group, (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5) with the mol ratio of tosic acid be 1:1.0, under the room temperature reaction obtain (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6); At last in the exsiccant methylene dichloride, under the room temperature through pyridinium chlorochromate (PCC) oxidation, (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6) with the mol ratio of PCC be 1:2.0, reaction finishes after diatomite filtration concentrates, column chromatography for separation obtains target product
1, productive rate is 90%.Above-mentioned each step reaction is followed the tracks of reaction process with thin layer plate.
Embodiment 2:
With 3-formyl radical-1, the 1'-binaphthol (
2) be raw material, it is dissolved in methyl alcohol, ice bath is cooled to 5 ℃ and adds sodium borohydride, 3-formyl radical-1, the mol ratio of 1'-binaphthol and sodium borohydride is 1.0:1.5, carries out reduction reaction under the room temperature, obtains 3-methylol-1, the 1'-binaphthol (
3); With acetone be then solvent under catalyzer (vitriol oil) condition, the described vitriol oil and 3-methylol-1, the 1'-binaphthol (
3) mol ratio 0.05:1, add 2, the 2'-Propanal dimethyl acetal, 3-methylol-1, the 1'-binaphthol (
3) with 2, the mol ratio of 2'-Propanal dimethyl acetal is 1.0:3.0, with organic solvent (ethyl acetate) extraction, concentrate behind the room temperature reaction, column chromatography for separation obtain product (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4), productive rate is 87%; Be solvent to do DMF then, ice bath adds sodium hydride down, react to add 3-(4-p-methoxy-phenyl)-urea groups-bromotoluene after 0.5 hour, (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4): the mol ratio of sodium hydride: 3-(4-methoxyl group-phenyl)-urea groups-bromotoluene is 1.0:1.2:1.3, room temperature reaction after column chromatography for separation obtain compound (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5), productive rate is 93%; Be solvent with ethylene glycol again, under the tosic acid effect, be heated to 50 ℃ and take off protecting group, (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5) with the mol ratio of tosic acid be 1:1.2, reaction obtain (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6); At last in the exsiccant methylene dichloride, under the room temperature through pyridinium chlorochromate (PCC) oxidation, (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6) with the mol ratio of PCC be 1:2.0, room temperature reaction finishes after diatomite filtration concentrates, column chromatography for separation obtains target product
1, productive rate is 90%.Above-mentioned each step reaction is followed the tracks of reaction process with thin layer plate.
Embodiment 3:
With 3-formyl radical-1, the 1'-binaphthol (
2) be raw material, it is dissolved in methyl alcohol, ice bath is cooled to 0 ℃ and adds sodium borohydride, 3-formyl radical-1, the mol ratio of 1'-binaphthol and sodium borohydride is 1.0:2.0, carries out reduction reaction under the room temperature, obtains 3-methylol-1, the 1'-binaphthol (
3); With acetone be then solvent under catalyzer (vitriol oil) condition, the vitriol oil and 3-methylol-1, the 1'-binaphthol (
3) mol ratio 0.03:1, add 2, the 2'-Propanal dimethyl acetal, 3-methylol-1, the 1'-binaphthol (
3) with 2, the mol ratio of 2'-Propanal dimethyl acetal is 1.0:4.0, with organic solvent (ethyl acetate) extraction, concentrate behind the room temperature reaction, column chromatography for separation obtain product (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4), productive rate is 90%; Be solvent to do DMF then, ice bath adds sodium hydride down, react to add 3-(4-p-methoxy-phenyl)-urea groups-bromotoluene after one hour, (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4): the mol ratio of sodium hydride: 3-(4-methoxyl group-phenyl)-urea groups-bromotoluene is 1.0:1.2:1.1, room temperature reaction after column chromatography for separation obtain compound (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5), productive rate is 90%; Be solvent with ethylene glycol again, under the tosic acid effect, be heated to 60 ℃ and take off protecting group, (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5) with the mol ratio of tosic acid be 1:1.2, reaction obtain (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6); At last in the exsiccant methylene dichloride, through pyridinium chlorochromate (PCC) oxidation, (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6) with the mol ratio of PCC be 1.0:2.5, reaction finishes after diatomite filtration concentrates under the room temperature, column chromatography for separation obtains target product
1, productive rate is 92%.Above-mentioned each step reaction is followed the tracks of reaction process with thin layer plate.
Embodiment 4
With 3-formyl radical-1, the 1'-binaphthol (
2) be raw material, it is dissolved in a certain amount of methyl alcohol, ice bath is cooled to 10 ℃ and adds sodium borohydride, 3-formyl radical-1, the mol ratio of 1'-binaphthol and sodium borohydride is 1.0:1.5, carries out reduction reaction under the room temperature, obtains 3-methylol-1, the 1'-binaphthol (
3); With acetone be then solvent under catalyzer (vitriol oil) condition, the vitriol oil and 3-methylol-1, the 1'-binaphthol (
3) mol ratio be 0.04:1, add 2, the 2'-Propanal dimethyl acetal, 3-methylol-1, the 1'-binaphthol (
3) with 2, the mol ratio of 2'-Propanal dimethyl acetal is 1.0:3.0, with organic solvent (ethyl acetate) extraction, concentrate behind the room temperature reaction, column chromatography for separation obtain product (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4), productive rate is 87%; Be solvent to do DMF then, ice bath adds sodium hydride down, react to add 3-(4-p-methoxy-phenyl)-urea groups-bromotoluene after one hour, (
S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
4): the mol ratio of sodium hydride: 3-(4-methoxyl group-phenyl)-urea groups-bromotoluene is 1.0:1.2:1.5, room temperature reaction after column chromatography for separation obtain compound (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5), productive rate is 95%; Be solvent with ethylene glycol again, under the tosic acid effect, be heated to 70 ℃ and take off protecting group, (
S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (
5) with the mol ratio of tosic acid be 1:1.1, under the room temperature reaction obtain (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6); At last in the exsiccant methylene dichloride, through pyridinium chlorochromate (PCC) oxidation, (
S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene (
6) with the mol ratio of PCC be 1.0:3.0, room temperature reaction finishes after diatomite filtration concentrates, column chromatography for separation obtains target product
1, productive rate is 95%.Above-mentioned each step reaction is followed the tracks of reaction process with thin layer plate.
Embodiment 5
Catalyzer among the foregoing description 1-embodiment 4 adopts tosic acid or PPTS; Organic solvent adopts methylene dichloride or chloroform..
Claims (4)
- One kind synthetic ( S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1, the method for 1'-dinaphthalene-3-formaldehyde is characterized in that: with 3-formyl radical-1, the 1'-binaphthol ( 2) be raw material, it is dissolved in methyl alcohol, ice bath is cooled to 0-10 ℃ and adds sodium borohydride, 3-formyl radical-1,1'-binaphthol (2) is 1.0:1.0 ~ 2.0 with the mol ratio of sodium borohydride, carries out 3-methylol-1 under the room temperature, the 1'-binaphthol ( 3); Be solvent then with acetone in the presence of, described and 3-methylol-1, the 1'-binaphthol ( 3) mol ratio 0.01:1-0.05:1 and catalyzer be a kind of among the vitriol oil, tosic acid and the PPTS, add 2, the 2'-Propanal dimethyl acetal, 3-methylol-1, the 1'-binaphthol ( 3) with 2, the mol ratio of 2'-Propanal dimethyl acetal is 1.0:2.0 ~ 4.0, reaction back organic solvent extraction is concentrated under the room temperature, column chromatography for separation obtain product ( S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene ( 4); Be solvent to do DMF then, ice bath adds sodium hydride down, and reaction 0.5～1 back adds 3-(4-p-methoxy-phenyl)-urea groups-bromotoluene, ( S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene ( 4): the mol ratio of sodium hydride: 3-(4-methoxyl group-phenyl)-urea groups-bromotoluene is 1.0:1.2:1.1 ~ 1.5, room temperature ( S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene ( 5); Be solvent again with ethylene glycol, take off protecting group for 50-70 ℃, ( S)-2-(3-phenyl urea groups benzyloxy)-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene ( 5) with the mol ratio of tosic acid be 1:1.0 ~ 1:1.2, under the room temperature ( S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene ( 6); At last in the exsiccant methylene dichloride, through the pyridinium chlorochromate oxidation, ( S)-2-hydroxyl-3-methylol-2'-(3-phenyl urea groups benzyloxy)-1, the 1'-dinaphthalene ( 6) with the mol ratio of pyridinium chlorochromate be 1:2.0 ~ 3., react under the room temperature, each step reaction is followed the tracks of reaction process with thin layer plate, then through diatomite filtration, concentrates, column chromatography for separation obtains target product, reaction formula is as follows:
。 - According to claim 1 described a kind of synthetic ( S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1, the method for 1'-dinaphthalene-3-formaldehyde is characterized in that: synthetic ( S)-2-hydroxyl-1-(2,2 ,-dimethyl-1,3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene ( 4) in the process with organic solvent extraction, when concentrating, described organic solvent is ethyl acetate or methylene dichloride or chloroform.
- A kind of synthesizing 3. according to claim 1 ( S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1, the method for 1'-dinaphthalene-3-formaldehyde is characterized in that: synthetic ( S)-2-hydroxyl-1-(2,2 ,-dimethyl-1, when 3-dioxy-1,2,3,4-tetrahydrochysene anthracene-9-)-naphthalene (4) institute to add catalyzer be the vitriol oil.
- A kind of synthesizing 4. according to claim 2 ( S)-2-hydroxyl-2'-(3-phenylurea benzyl)-1, the method for 1'-dinaphthalene-3-formaldehyde is characterized in that: described organic solvent is an ethyl acetate.
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| CN2010105930013A CN102070492B (en) | 2010-12-17 | 2010-12-17 | Method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde |
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| CN2010105930013A CN102070492B (en) | 2010-12-17 | 2010-12-17 | Method for synthesizing (S)-2-hydroxy-2'-(3-phenylureaphenyl)-1,1'-binaphthyl-3-formaldehyde |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617310A (en) * | 2012-03-01 | 2012-08-01 | 天津市炜杰科技有限公司 | Adamantane formaldehyde synthetic method suitable for industrial production |
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Non-Patent Citations (3)
| Title |
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| HYUNJUNG PARK，ET AL: "Stereoconversion of Amino Acids and Peptides in Uryl-Pendant Binol Schiff Bases", 《CHEM. EUR. J.》 * |
| KWAN MOOK KIM，ET AL: "Enantioselective Recognition of 1,2-Amino Alcohols by Reversible Formation of Imines with Resonance-Assisted Hydrogen Bonds", 《ORGANIC LETTERS》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102617310A (en) * | 2012-03-01 | 2012-08-01 | 天津市炜杰科技有限公司 | Adamantane formaldehyde synthetic method suitable for industrial production |
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