134931-64-9

Basic information

• Product Name: methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate
• Synonyms: methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate
• CAS NO: 134931-64-9
• Molecular Weight: 208.214
• Mol File: 134931-64-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate(134931-64-9)
• EPA Substance Registry System: methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate(134931-64-9)

Safety Data

• Hazardous Substances Data: 134931-64-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 81860-68-6 3-(4-methoxyphenyl)-oxiranecarbonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 96-34-4 methyl chloroacetate 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 19310-29-3 3-(4-methoxyphenyl)acrylic acid methyl ester 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 

Downstream Products

• 76436-36-7 trans-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one 
• 76436-36-7 cis-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one 
• 195616-20-7 (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide 
• 42399-49-5 (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 
• 97652-92-1 methyl 2-hydroxy-3-methoxy-3-(4-methyoxyphenyl)propionate 
• 23515-44-8 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 222292-12-8 (2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 27068-88-8 3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 30193-56-7 3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 30193-56-7 methyl threo-2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionate 
• 27068-88-8 (+/-)-trans-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 30067-00-6 (2RS,3SR)-2-hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylsulfanyl)-propionic acid methyl ester 
• 30067-00-6 methyl (2RS,3RS)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate 

Relevant articles and documents

Enantioselective Darzens reaction: Asymmetric synthesis of trans-glycidic esters mediated by chiral lithium amides

Enantioselective and diastereoselective Darzens reaction mediated by chiral lithium amides was achieved between tert-butyl chloroacetate and aromatic aldehydes to give the corresponding trans-glycidic esters in up to 84% enantiomeric excess.

Efficient alternative synthetic route to diltiazem via (2R,3S)-3-(4- methoxyphenyl)glycidamide

An effective new route to diltiazem, a representative coronary vasodilator, through (-)-(2R,3S)-3-(4-methoxyphenyl)glycidamide [(-)-2] has been achieved. The glycidamide (-)-2 was prepared in 43% overall yield by a combination of the enzymatic resolution of methyl (±)2(2RS,3SR)-3-(4- methoxyphenyl)glycidate [(±)-1] with lipase and the following amidation of (-)-1 with ammonia. A one-pot synthesis through the treatment of (-)-2 with 2-aminothiophenol and a following ring closing reaction efficiently gave a key intermediate of diltiazem synthesis, (2S,3S)-2,3-dihydro-3-hydroxy-2-(4- methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [cis-(+)-5] in 80% overall yield.

Reactions of Methyl threo-2-Acetoxy-3-chloro-3-(4-methoxyphenyl)propanoate and Methyl cis-2,3-Epoxy-3-(4-methoxyphenyl)propanoate with 3,5-Dimethoxyphenol: Potential Routes to Flavan-3-ols

Attempted syntheses of flavan-3-ols by reaction of either methyl threo-2-acetoxy-3-chloro-3-(4-methoxyphenyl)propanoate (3) or methyl cis-2,3-epoxy-3-(4-methoxyphenyl)propanoate (14) with 3,5-dimethoxyphenol failed to give the required aryl ethers.Products usually were derived from C-alkylation of the electron-rich phenol although reaction of the chloro acetate (3) with the phenoxide ion gave the furanone (5).The single-crystal X-ray structures of methyl 4-hydroxy-3-(4-methoxyphenyl)-2-(4-methoxyphenylmethyl)-5-oxo-2,5-dihydrofuran-2-carboxylate and cis-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one have been determined.