134931-62-7

Basic information

• Product Name: methyl (2S,3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate
• Synonyms: methyl (2S,3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate
• CAS NO: 134931-62-7
• Molecular Weight: 244.675
• Mol File: 134931-62-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl (2S,3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S,3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate(134931-62-7)
• EPA Substance Registry System: methyl (2S,3S)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate(134931-62-7)

Safety Data

• Hazardous Substances Data: 134931-62-7(Hazardous Substances Data)

Upstream product

• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 22027-50-5 methyl 3-(4-methoxybenzoyl)acetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 78437-40-8 methyl 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate 

Downstream Products

• 105560-93-8 methyl (2R,3S)-3-(4-methoxyphenyl)glycidate 

Relevant articles and documents

Highly enantioselective Mukaiyama aldol reaction of αα-dichloro ketene silyl acetal: An efficient synthesis of a key intermediate for diltiazem

An efficient synthesis of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (-)-2, a key intermediate for diltiazem (1), has been developed on the basis of the highly enantioselective Mukaiyama aldol reaction of p-anisaldehyde (4a) with αα-dichloro ketene silyl acetal 5. Thus, the reaction using a stoichiometric amount of chiral oxazaborolidinone catalyst 12a proceeded to excellent yield (83%) and high enantioselectivity (96% ee), together with the chiral ligand 13a in nearly quantitative recovery. The reaction using a substoichiometric amount of 12e (20 mol%) also proceeded to excellent yield (88%), with somewhat lower enantioselectivity (77% ee). The aldol product 3a thus obtained was easily converted to (-)-2 in excellent yield (80%) and high optical purity (>99% ee). The highly enantioselective Mukaiyama aldol reaction with 5 catalyzed by 12a proved to be applicable to various aldehydes. An efficient preparation of 5 from inexpensive starting materials was also described.

A new enantioselective synthesis of glycidates via dynamic kinetic resolution of racemic 2-chloro-3-keto esters using chiral Ru (II) complexes

2-chloro-3-keto esters were quantitatively hydrogenated to syn and anti 2-chloro-3-hydroxyester by asymmetric hydrogenation with chiral ruthenium (II) catalysts prepared in-situ from (COD)Ru(2-methylallyl)2 in presence of atropisomeric ligands such as MeO-Biphep and Binap, giving enantioselectivity up to 99%, 2-chloro-3-hydroxy esters were treated with different bases to give (E)-and (Z)-2,3-epoxyalkanoates in 65-90% yields with 84-97% ee.