129866-71-3

Basic information

• Product Name: Methyl (2S,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate
• Synonyms: Methyl (2S,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate
• CAS NO: 129866-71-3
• Molecular Weight: 221.216
• Mol File: 129866-71-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Methyl (2S,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (2S,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate(129866-71-3)
• EPA Substance Registry System: Methyl (2S,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate(129866-71-3)

Safety Data

• Hazardous Substances Data: 129866-71-3(Hazardous Substances Data)

Upstream product

• 115794-66-6 trans-methyl 3-phenylglycidate 
• 121-39-1 ethyl 3-phenylglycidate 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 100-52-7 benzaldehyde 
• 103-26-4 Methyl cinnamate 
• 129939-42-0 Sodium (+)-(2S,3R)-E-3-phenyl oxirane-2-carboxylate 
• 328402-02-4 (2R,3S)-2-Acetoxy-3-chloro-3-phenyl-propionic acid methyl ester 
• 145438-00-2 methyl (+/-)-syn-3-chloro-2-hydroxy-3-phenylpropanoate 
• 145438-00-2 methyl (+/-)-anti-3-chloro-2-hydroxy-3-phenylpropanoate 
• 328402-06-8 (2R,3R)-2-Acetoxy-3-chloro-3-phenyl-propionic acid methyl ester 
• 32803-73-9 methyl 3-phenyl-3-chloro-2-ketopropionate 
• 328402-07-9 methyl (2R,3R)-3-chloro-2-hydroxy-3-phenylpropanoate 

Downstream Products

• 150949-07-8 methyl (2S,3S)-phenylisoserine 
• 129939-52-2 Methyl (2R,3S)-3-phenyl-1H-aziridine-2-carboxylate 
• 129866-73-5 (2R,3S)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester 
• 144541-45-7 methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 146848-91-1 (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 158830-39-8 methyl (2S,3S)-2-hydroxy-3-(N-tert-butoxycarbonylamino)-3-phenylpropanoate 
• 119628-74-9 cis-(4S,5S)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 

Relevant articles and documents

Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: Hemisynthesis of Taxotere through Ru-DIFLUORPHOS asymmetric hydrogenation

The dynamic kinetic resolution (DKR) of racemic α-chloro β-ketoesters and α-chloro β-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding α-chloro β-hydroxyesters and α-chloro β- hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, 13C NMR in chiral oriented solvents was used to investigate the DKR effect.

CHEMO-ENZYMATIC SYNTHESIS OF ALL ISOMERIC 3-PHENYLSERINES AND -ISOSERINES

The synthesis of all isomers of 3-phenylserines and 3-phenylisoserines in enantiomerically pure form is presented.Diastereomerically pure educts (threo/erythro-2-azido-3-butanoyloxy-3-phenyl-propionic esters, threo/erythro-3-azido-2-butanoyloxy-3-phenylpropionic esters, threo-2-butanoylamino-3-butanoyloxy-3-phenylpropionic ester, erythro-3-butanoylamino-2-butanoyloxy-3-phenyl-propionamide) were prepared from cinnamic acid derivatives or via aldol condensations of benzaldehyde and suitable enolates in few steps.These racemates were resolved with lipases from Candida cylindracea (CC) and Pseudomonas fluorescens (P) and the obtained products were hydrogenated to 3-phenylserines and -isoserines.The influence of the acyl group in the enzymatic resolution of erythro-3-azido-2-acyloxy-3-phenylpropionic esters was investigated.