Methyl (2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate

Base Information

• Chemical Name: Methyl (2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate
• CAS No.: 105560-93-8
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• Hs Code.: 2918990090
• European Community (EC) Number: 404-130-2
• UNII: D8MQ7L5PJ2
• DSSTox Substance ID: DTXSID40232949
• Nikkaji Number: J547.196F
• Wikidata: Q83114186
• Mol file: 105560-93-8.mol

Synonyms:3-(-methoxyphenyl)glycidic acid methylester;methyl (2R,3S)-3-(4-methoxyphenyl)glycidate;methyl 2,3-epoxy-3-(4-methoxyphenyl)propionate;methyl 3-(4-methoxyphenyl)glycidate;methyl-3-(4-methoxyphenyl)glycidate;t-methyl-3-phenylglycidate

Chemical Property of Methyl (2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate

Chemical Property:

• Appearance/Colour: White fine crystals
• Vapor Pressure: 0.00133mmHg at 25°C
• Melting Point: 87-88 °C
• Refractive Index: 1.534
• Boiling Point: 297.721 °C at 760 mmHg
• Flash Point: 129.237 °C
• PSA: 48.06000
• Density: 1.224 g/cm₃
• LogP: 1.30810
• 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:

99.9% ^*data from raw suppliers

Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41-43-52/53
• Safety Statements: 24-26-37/39-61

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
• Uses: Methyl (-?)?-?(2R,?3S)?-?2,?3-?epoxy-?3-?(4methoxyphenyl)?propronate is a chiral intermediate and is prepared using newly isolated Galactomyces geotrichum.

Technology Process of Methyl (2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate

There total 61 articles about Methyl (2R,3S)-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: 90.0%

methyl (2S,3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate (134931-62-7) → methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (105560-93-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/0040-4039(95)00182-C

Reference yield: 83.0%

methanol (67-56-1) + (-)-(2R,3S)-sodium 3-(4-methoxyphenyl)glycidate (136597-65-4) → methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (105560-93-8)

Guidance literature:

With triethylamine; 2-chloro-1-methylpyridinium sulfate; In dichloromethane; 1,2-dichloro-ethane; Ambient temperature;

DOI:10.1016/S0957-4166(00)82162-X

Reference yield: 81.0%

(S)-2-Chloro-3-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester (336113-23-6) → methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (105560-93-8)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.mcat.2021.111670

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

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

(2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester

Refernces

• 1、 Seki, Masahiko,Furutani, Toshiyuki,Imashiro, Ritsuo,Kuroda, Tooru,Yamanaka, Takeshi,Harada, Naoyuki,Arakawa, Hiroaki,Kusama, Mari,Hashiyama, Tomiki. "A novel synthesis of a key intermediate for diltiazem". . p. 8201 - 8205. Retrieved 2001.
• 2、 Chen, Cheng,Chen, Qi,Ni, Guo-Wei,Pan, Jiang,Xu, Jian-He,Xuan, Yang. "Asymmetric reduction of 2-chloro-3-oxo-ester into enantiomerically high pure diltiazem precursor by a Candida ketoreductase". . . Retrieved 2021.
• 3、 Gentile,Giordano,Fuganti,Ghirotto,Servi. "The enzymatic preparation of (2R,3S) phenyl glycidic acid esters". . p. 6635 - 6635. Retrieved 1992.
• 4、 Wilcke, David,Bach, Thorsten. "Sc(OTf)3-catalyzed diastereoselective Friedel-Crafts reactions of arenes and hetarenes with 3-phenylglycidates". supporting information; experimental part. p. 6498 - 6503. Retrieved 2012/09/08.