135821-94-2

Basic information

• Product Name: methyl (2S,3R)-3-benzoylamino-2-hydroxy-3-phenylpropionate
• Synonyms: methyl (2S,3R)-3-benzoylamino-2-hydroxy-3-phenylpropionate
• CAS NO: 135821-94-2
• Molecular Weight: 299.326
• Mol File: 135821-94-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: methyl (2S,3R)-3-benzoylamino-2-hydroxy-3-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S,3R)-3-benzoylamino-2-hydroxy-3-phenylpropionate(135821-94-2)
• EPA Substance Registry System: methyl (2S,3R)-3-benzoylamino-2-hydroxy-3-phenylpropionate(135821-94-2)

Safety Data

• Hazardous Substances Data: 135821-94-2(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 322407-45-4 (+)-(2S,3R)-methyl 3-amino-2-hydroxy-3-phenylpropanoate 
• 780721-69-9 3-Amino-2-hydroxy-3-phenyl-propionic acid methyl ester 
• 1452586-41-2 methyl (4R,5S)-3-benzoyl-4-phenyloxazolidin-2-one-5-carboxylate 
• 4461-33-0 benzoyl isocyanate 
• 115794-67-7 methyl (2R,3S)-3-phenylglycidate 
• 103-26-4 Methyl cinnamate 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 135787-47-2 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(3S,4R)-3-(4-methoxy-phenoxy)-2-oxo-4-phenyl-azetidin-1-yl]-tetrahydro-pyran-3-yl ester 
• 94388-46-2 2,3,4,6-Tetra-O-acetyl-β-D-galactoseamine benzaldimine 
• 14990-09-1 tert-butyl cinnamate 
• 51608-62-9 (E)-N-benzylidenebenzamide 
• 151764-53-3 (2R,3R)-(-)-2-hydroxy-3-(benzoylamino)-3-phenylpropanoic acid methyl ester 
• 151671-03-3 tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate 

Downstream Products

• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 7309-55-9 N-benzoyl-(2R^*,3S^*)-3-phenylisoserine 

Relevant articles and documents

Chiral Auxiliary-Mediated Asymmetric Induction in a Thermal Inverse Electron Demand Hetero-Diels-Alder Reaction. Enantioselective Synthesis of the Taxol A-Ring Side Chain

Chiral auxiliary-modified ketene acetal 5g and N-benzoylbenzaldimine (4) engage in an endo and ?-facially selective thermal inverse electron demand hetero-Diels-Alder reaction that is the key step in a synthesis of enantiomerically pure taxol A-ring side-chain methyl ester 9.

Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters

A novel efficient method was proposed for the synthesis of enantiopure precursors of taxane-containing cytostatics, i.e., methyl esters of (2R,3S)- and (2S,3R)-N-benzoylphenylisoserine and similar taxoid esters. The method is based on the regio- and stereoselective hydrobromolysis of the corresponding trans-β-phenyl glycidate enatiomers, consecutive reactions of O-acylcarbamoylation of the obtained 3-bromohydrins, intramolecular cyclization to 4-phenyloxazolidin-2-one-5-carboxylic acid derivatives, and oxazolidinone ring opening.

A practical and stereoselective synthesis of taxol side chain

Apractical and efficient synthesis of taxol C-13 side chain from cheap and easily available starting material is described.