137173-40-1

Basic information

• Product Name: Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, methyl ester, (2S,3R)-
• CAS NO: 137173-40-1
• Molecular Formula: C11H12O4
• Molecular Weight: 208.214
• Mol File: 137173-40-1.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, methyl ester, (2S,3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, methyl ester, (2S,3R)-(137173-40-1)
• EPA Substance Registry System: Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, methyl ester, (2S,3R)-(137173-40-1)

Safety Data

• Hazardous Substances Data: 137173-40-1(Hazardous Substances Data)

Upstream product

• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 108-93-0 cyclohexanol 
• 78-92-2 iso-butanol 
• 42245-42-1 methyl 3-(4-methoxyphenyl)glycidate 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 111-87-5 octanol 
• 71-36-3 butan-1-ol 
• 27331-97-1 ethyl α-hydroxyimino-β-oxo-4-methoxybenzenepropionate 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 96-34-4 methyl chloroacetate 
• 67-56-1 methanol 
• 800368-85-8 (2R,3R)-methyl 3-hydroxy-2-iodo-3-(4-methoxyphenyl)-propanoate 

Downstream Products

• 134931-64-9 methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate 
• 23515-44-8 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 97652-92-1 methyl 2-hydroxy-3-methoxy-3-(4-methyoxyphenyl)propionate 
• 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 
• 856899-98-4 methyl 2-dihydroxy-3-(4-methoxyphenyl)propanoate 
• 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 

Relevant articles and documents

Lewis acid catalyzed asymmetric halohydrin reactions of chiral α,β-unsaturated carboxylic acid derivatives with N-halosuccinimide (NXS) as the halogen source

Lewis acid catalyzed asymmetric halohydrin reactions-(halohydroxylation as well as halomethoxylation) of chiral α,β-unsaturated carboxylic acid derivatives were performed using N-halosuccinimide (NXS; X = Br, I) as the halogen source. Regio- and anti-sele

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.

Gelozymes in organic synthesis. Part IV: Resolution of glycidate esters with crude Mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in gelatin matrix

A crude extract of Mung bean meal (Phaseolus radiatus) possessing epoxide hydrolase activity immobilized in gelatin gel (gelozyme) is employed in the stereoselective epoxide ring opening of glycidate esters. Thus, ethyl trans-(±)-3-phenyl glycidate 1a and methyl trans-(±)-3-(4-methoxyphenyl) glycidate 1b gave (2S,3R)-glycidate esters (ee >99% and 45% yield) with gelatin immobilized enzyme in diisopropyl ether. The corresponding (2R,3S)-enantiomer of 1a was hydrolyzed by an epoxide hydrolase to predominantly give the anti-product, ethyl (2R,3R)-2,3-dihydroxy-3-phenylpropanoate, with a diastereomeric excess of 78% and ee 94% (40%). A small amount (5%) of racemic syn-product was also obtained as a result of the spontaneous hydrolysis. In the case of 1b, the hydrolysis product was racemic due to high reactivity of the glycidate toward water.