126060-70-6

Basic information

• Product Name: (2R,3R)-3-(4-Methoxy-phenyl)-oxirane-2-carboxylic acid methyl ester
• Synonyms: (2R,3R)-3-(4-Methoxy-phenyl)-oxirane-2-carboxylic acid methyl ester
• CAS NO: 126060-70-6
• Molecular Weight: 208.214
• Mol File: 126060-70-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2R,3R)-3-(4-Methoxy-phenyl)-oxirane-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-3-(4-Methoxy-phenyl)-oxirane-2-carboxylic acid methyl ester(126060-70-6)
• EPA Substance Registry System: (2R,3R)-3-(4-Methoxy-phenyl)-oxirane-2-carboxylic acid methyl ester(126060-70-6)

Safety Data

• Hazardous Substances Data: 126060-70-6(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 96-34-4 methyl chloroacetate 
• 67-56-1 methanol 
• 81860-68-6 3-(4-methoxyphenyl)-oxiranecarbonitrile 
• 122517-80-0 (2S,3R)-(-)-methyl 2,3-dihydroxy-3-(p-methoxyphenyl)propionate 
• 206346-47-6 (2S,3R)-2-Acetoxy-3-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 106146-94-5 methyl 2,3-dihydroxy-3-(4-methoxyphenyl)propanoate 
• 132377-68-5 (2S,3R)-(-)-methyl 3-hydroxy-3-(p-methoxyphenyl)-2-((p-tolylsulfonyl)oxy)propionate 
• 127347-52-8 (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(2,4,6-trichloro-benzenesulfonyloxy)-propionic acid methyl ester 
• 19310-29-3 3-(4-methoxyphenyl)acrylic acid methyl ester 

Downstream Products

• 134931-64-9 methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate 
• 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 
• 195616-20-7 (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide 
• 222292-12-8 (2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 42399-49-5 (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 
• 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 
• 76436-36-7 cis-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one 
• 76436-36-7 trans-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one 

Relevant articles and documents

Sc(OTf)3-catalyzed diastereoselective Friedel-Crafts reactions of arenes and hetarenes with 3-phenylglycidates

Five different para-substituted 3-phenylglycidates (3-phenyloxirane-2- carboxylates) were prepared and subjected to reactions with arenes and hetarenes under Lewis acid catalysis. Sc(OTf)3 was found to effectively (5 mol%) promote a Friedel-Crafts reaction in nitromethane as the solvent. The reaction was shown to proceed stereoconvergently, which makes the intermediacy of a benzylic cation likely. The diastereoselectivities varied depending on the choice of the nucleophile and 3-arylglycidate. Best results were obtained with tert-butyl 3-anisylglycidate, which delivered the respective products with high syn-preference in diastereomeric ratios (d.r.) between 82:18 and >95:5. The observed selectivity can be explained by a model, according to which the intermediate benzylic cations adopt a preferred conformation, which allows for diastereoface-differentiation by the adjacent stereogenic center.

Synthesis of taxoids II. Synthesis and antitumor activity of water-soluble taxoids

Synthesis of novel taxoid water-soluble prodrugs that have 2′-substituted amino acid derivatives with spacer is described. Enantioselective synthesis of the C-13 side chains proceeded through the asymmetric dihydroxylation. Several compounds had good solubility in saline and showed potent antitumor activity against B16 melanoma in mice.

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.