Methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate, (+/-)-

Base Information

• Chemical Name: Methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate, (+/-)-
• CAS No.: 137173-40-1
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• European Community (EC) Number: 404-130-2
• UNII: VT0V507XJB,LQ65CA9BKC
• Nikkaji Number: J576.235I
• Mol file: 137173-40-1.mol

Synonyms:Methyl trans-3-(4-methoxyphenyl)glycidate;LQ65CA9BKC;VT0V507XJB;137173-40-1;methyl (2S,3S)-3-(4-methoxyphenyl)oxirane-2-carboxylate;Methyl 3-(4-methoxyphenyl)glycidate, trans-(+)-;Methyl 3-(4-methoxyphenyl)glycidate, trans-(+/-)-;Methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate, (+/-)-;Methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate, (2R,3S)-(+)-;2-Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, methyl ester, (2R,3S)-rel-;2-Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, methyl ester, (2S,3R)-;Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, methyl ester, trans-(+/-)-;96125-49-4;UNII-VT0V507XJB;105560-93-8;UNII-LQ65CA9BKC;METHYL (2R,3S)-2,3-EPOXY-3-(4-METHOXYPHENYL)PROPIONATE;SCHEMBL7141149;CVZUMGUZDAWOGA-ZJUUUORDSA-N;Methyl trans-3-(4-methoxyphenyl)glycidate, 97%;(2s,3r)-3-(4-methoxyphenyl)glycidic acid methyl ester;(2S,3R)-methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate

Chemical Property of Methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate, (+/-)-

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 208.07355886
• Heavy Atom Count: 15
• Complexity: 233

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2C(O2)C(=O)OC
• Isomeric SMILES: COC1=CC=C(C=C1)[C@@H]2[C@H](O2)C(=O)OC

Technology Process of Methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate, (+/-)-

There total 43 articles about Methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate, (+/-)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

methyl (2-RS,3-SR)-3-hydroxy-3-(4-methoxyphenyl)-2-<(4-methoxyphenyl)sulfonyloxy>propanoate → methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate (42245-42-1,84056-02-0,84976-49-8,88877-35-4,96125-49-4,105560-93-8,126060-70-6,134931-64-9,137173-40-1)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; for 1h; Ambient temperature;

Reference yield: 76.0%

3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3) + butan-1-ol (71-36-3) → methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (105560-93-8) + (2S,3R)-trans-(4-methoxyphenyl)glycidic acid butyl ester (139345-88-3) + (2S,3R)-methyl p-methoxycinnamate epoxide (137173-40-1)

Guidance literature:

3-(4-methoxy-phenyl)acrylic acid methyl ester; With Oxone; (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid cyclic ester; In 1,4-dioxane; water; for 26h;

butan-1-ol; With Serratia marcescens lipase on celit; for 25h; Further stages.;

DOI:10.1021/jo025647b

Reference yield: 74.0%

methyl (2S,3S)-(+)-2-bromo-3-hydroxy-3-(4-methoxyphenyl)propionate (153829-67-5) → methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (105560-93-8) + (2S,3R)-methyl p-methoxycinnamate epoxide (137173-40-1)

Guidance literature:

With potassium carbonate; In methanol; diethyl ether; at 0 - 5 ℃; for 0.5h; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1248/cpb.41.1521

upstream raw materials:

methanol

3-(4-methoxyphenyl)-oxiranecarbonitrile

4-methoxy-benzaldehyde

methyl chloroacetate

Downstream raw materials:

trans-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one

cis-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one

methyl 2-dihydroxy-3-(4-methoxyphenyl)propanoate

methyl 2-hydroxy-3-methoxy-3-(4-methyoxyphenyl)propionate

Refernces

• 1、 Wei, Chun,Ling, Jinlong,Shen, Honglei,Zhu, Qing. "Bioresolution production of (2R,3S)-Ethyl-3-phenylglycidate for chemoenzymatic synthesis of the taxol C-13 side chain by galactomyces geotrichum ZJUTZQ200, a new epoxide-hydrolase-producing strain". . p. 8067 - 8079. Retrieved 2014/07/08.
• 2、 Zhao, Jing,Chu, Yan-Yan,Li, Ai-Tao,Ju, Xin,Kong, Xu-Dong,Pan, Jiang,Tang, Yun,Xu, Jian-He. "An unusual (R)-selective epoxide hydrolase with high activity for facile preparation of enantiopure glycidyl ethers". experimental part. p. 1510 - 1518. Retrieved 2011/08/03.