126015-22-3

Basic information

• Product Name: (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester
• Synonyms: (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester
• CAS NO: 126015-22-3
• Molecular Weight: 343.379
• Mol File: 126015-22-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester(126015-22-3)
• EPA Substance Registry System: (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester(126015-22-3)

Safety Data

• Hazardous Substances Data: 126015-22-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 126061-52-7 [(1S,2R)-1-Benzyl-2-cyano-2-((1R,3R)-3-hydroxy-1-methyl-butoxy)-ethyl]-carbamic acid benzyl ester 
• 126015-21-2 [(1S,2R)-1-Benzyl-2-cyano-2-((1S,3S)-3-hydroxy-1-methyl-butoxy)-ethyl]-carbamic acid benzyl ester 
• 686343-71-5 (1S,2RS)-[1-benzyl-3-(diphenyl-phosphinoyl)-2-hydroxy-3,3-dimethoxy-propyl]carbamic acid benzyl ester 
• 113283-75-3 [(S)-1-((4S,6S)-4,6-Dimethyl-[1,3]dioxan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 113283-78-6 [(S)-1-((4R,6R)-4,6-Dimethyl-[1,3]dioxan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 114744-85-3 [(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 
• 214122-05-1 (4S)-4-[[(benzyloxy)carbonyl]amino]-3-oxo-5-phenyl-2-triphenylphosphoranylidene-pentanenitrile 
• 1161-13-3 N-Cbz-L-Phe 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 116565-10-7 (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 501-53-1 benzyl chloroformate 
• 157683-55-1 (3S)-3-[[(benzyloxy)carbonyl]amino]-2-oxo-4-phenylbutanoic acid methyl ester 

Downstream Products

• 165187-26-8 Methyl-N-benzyloxycarbonyl-3(S)-amino-2(R)-p-toluenesulfonyloxy-4-phenylbutyrate 
• 322729-66-8 (2R,3S)-2-hydroxy-4-phenyl-3-[[[3-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 
• 322729-60-2 (2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 
• 322729-68-0 (3S)-2-oxo-4-phenyl-3-[[[3-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 
• 322729-62-4 (3S)-2-oxo-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 
• 181047-32-5 (2S,3S)-3-Benzyloxycarbonylamino-2-fluoro-4-phenyl-butyric acid methyl ester 
• 62023-60-3 (2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid 

Relevant articles and documents

A convenient preparation of (2SR,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid; an important peptide bond isostere

We present an efficient synthesis of N-Z-(2SR,3S)-3-amino-2-hydroxy-4- phenylbutanoic acids by hydroxylation of an enolate derived from methyl (3S)N-Z-3-amino-4-phenylbutanoate with oxodiperoxymolybdenum (pyridine) (hexamethyl phosphoric triamide) complex

Acylation of alkyl halides and amino aldehydes with a phosphane oxide-based d1-synthon

Alkyl iodides and α-amino aldehydes can be homologated to the corresponding methyl esters and β-amino methyl esters, including β-amino-α-hydroxy methyl esters, using lithiated (dimethoxymethyl) diphenylphosphane oxide. The primary α,α-(dimethoxy) diphenylphosphane oxides obtained by this Horner-Wittig type process collapse to give the target esters under proton-catalyzed conditions in the presence of water. Detailed and carefully conducted mechanistic studies revealed that the diphenylphosphane oxide group is activated by protonation, and acts as the initial leaving group in this process. In the cases of adducts derived from the reaction of the phosphane oxide-stabilized anion with α-amino aldehydes, homologation to the β-amino- and β-amino-α-hydroxy methyl esters can be achieved by KOtBu-mediated elimination to the intermediate O,O-ketene acetals. These may either be allowed to react with water under acidic conditions to yield the β-amino methyl esters, or may be treated under the Sharpless asymmetric dihydroxylation conditions to directly furnish the β-amino-α-hydroxy methyl esters. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Azobenzene-containing, peptidyl α-ketoesters as photobiological switches of α-chymotrypsin

Three photoswitchable, peptidomimetic inhibitors of α-chymotrypsin have been synthesised. The compounds comprise an azobenzene, an α-ketoester and L-phenylalanine. The compounds were photoisomerised to give enriched states of the (E) and (Z) isomers and t