147058-27-3

Basic information

• Product Name: methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate
• Synonyms: methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate
• CAS NO: 147058-27-3
• Molecular Weight: 299.37
• Mol File: 147058-27-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate(147058-27-3)
• EPA Substance Registry System: methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate(147058-27-3)

Safety Data

• Hazardous Substances Data: 147058-27-3(Hazardous Substances Data)

Upstream product

• 1310-73-2 sodium hydroxide 
• 154306-81-7 (3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one 
• 67-56-1 methanol 
• 1254191-15-5 C₂₅H₃₃NO₅ 
• 69350-13-6 N-benzylidene-(S)-α-methylbenzylamine 
• 212764-79-9 methyl (2R,3S)-2-methoxy-3-phenyl-3-<(S)-methylbenzylamino>propanoate 
• 150811-50-0 (E)-((2-((tert-butyldimethylsilyl)oxy)-1-methoxyvinyl)oxy)trimethylsilane 

Downstream Products

• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 153652-71-2 (4S,5R)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 

Relevant articles and documents

A highly diastereoselective synthesis of α-hydroxy-β-amino acid derivatives via a Lewis acid catalyzed three-component condensation reaction

A very efficient three-component synthesis of a series of syn α-hydroxy-β-amino esters, obtained in high diastereoselection and yield, was realized starting from an aldehyde, benzylamine, and the ketene silyl acetals derived from Ley's lactones. The synthetic protocol was optimized and the above compounds were obtained without the isolation of intermediates. The origin of the observed diastereoselection was investigated through a computational model of the key reaction step.

Practical synthesis of taxol side chain

Practical large scale synthesis of N-benzoyl-(2R,3S)-phenylisoserine methyl ester of the Taxol side chain has been attained from the coupling of chiral imine of N-[(S)-methylbenzyl]benzaldimine with (Z)-α-methoxy trimethylsilyl ketene acetal followed by the sequential reactions of lactamization, demethylation, methanolysis and N-benzoylation.

Method for the preparation of β-phenylisoserine derivatives

Method for the preparation of β-phenylisoserine derivatives of general formula (I) involving the action of an anhydride and hydrogen with a product of general formula (II). The products of general formula (I) are especially useful in the preparation of taxoids having outstanding antitumour properties. In general formulae (I) and (II), Ar is an aryl radical, Ph is a phenyl radical or an optionally substituted α or β-naphtyl, R is a hydrogen atom or an alkyl radical optionally substituted by a phenyl radical and R1 is an optionally substituted phenyl radical or a R2 --O radical wherein R2 is an alkyl, alkenyl, cycloalkyl, phenyl or heterocyclyl. STR1