139069-60-6

Basic information

• Product Name: (3S,2S)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester
• Synonyms: (3S,2S)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester
• CAS NO: 139069-60-6
• Molecular Weight: 209.245
• Mol File: 139069-60-6.mol

Chemical Properties

• CAS DataBase Reference: (3S,2S)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,2S)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester(139069-60-6)
• EPA Substance Registry System: (3S,2S)-3-amino-2-hydroxy-4-phenylbutyric acid methyl ester(139069-60-6)

Safety Data

• Hazardous Substances Data: 139069-60-6(Hazardous Substances Data)

Upstream product

• 37779-49-0 methyl 3-oxo-4-phenylbutanoate 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 186393-18-0 ((S)-1-benzyl-2-cyano-2-hydroxy-ethyl)-carbamic acid tert-butyl ester 
• 191849-93-1 3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid 
• 209173-80-8 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 72155-45-4 Boc-L-phenylalaninal 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 5123-55-7 Nα-phthaloyl-L-phenylalanine 
• 55722-86-6 (2S)-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanal 
• 63-91-2 L-phenylalanine 
• 150095-78-6 (2S,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-hydroxy-4-phenyl-butyric acid methyl ester 
• 116565-03-8 N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 

Downstream Products

• 139694-65-8 (S)-N-tert-butyl-3-[(2S,3S)-2-hydroxy-3-[(S)-2-benzyloxycarbonylaminosuccinamyl]amino-4-phenylbutanoyl]pyrrolidine-2-carboxamide 
• 141171-77-9 (S)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(1-naphthoxyacetyl)aminosuccinamyl]amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carboxamide 
• 153380-41-7 (S)-2-Amino-N¹-[(1S,2S)-1-benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-succinamide 
• 143978-10-3 Z-Asn-(2S,3S)-AHPBA-OH 
• 140409-02-5 methyl (2S,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate 
• 140409-03-6 methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate 
• 59554-14-2 DL-erythro-3-amino-2-hydroxy-4-phenylbutanoic acid 
• 59554-14-2 (±)-(4R,5S)-4-benzyl-2-oxooxazolidine-5-carboxylic acid 

Relevant articles and documents

A case study of the MAC (masked acyl cyanide) oxyhomologation of N, N -dibenzyl-l-phenylalaninal with anti diastereoselectivity: Preparation of (2 S,3 S)-allophenylnorstatin esters

The three-component reaction between a protected α-amino aldehyde, an alcohol and an α-silyloxymalononitrile provides an expedient access to protected α-hydroxy-β-amino acid derivatives. The prototypical process, performed on N-Cbz-phenylalaninal, is known to proceed with syn diastereoselectivity. The present study demonstrates that the diastereoselectivity of the reaction can be inverted, using the rationale of a Felkin-Anh interaction model. Reactions performed on N,N-dibenzyl-l-phenylalaninal proceed with a high anti diastereoselectivity, providing a panel of synthetically useful ester derivatives of (2S,3S)-allophenylnorstatin. The procedure is exploited to accomplish one of the most efficient syntheses of the title compound to date, in 3 steps (66% yield) from N,N-dibenzyl-l-phenylalaninal.

Diastereoselective approach to an HIV protease inhibitor intermediate using a cation-exchange resin mediated Mannich-type reaction

Mannich-type reaction of ketene silyl acetals with a chiral imine proceeded smoothly to give β-amino esters in good yields with high diasetereoselectivity under the influence of a cation-exchange resin, and the subsequent functional group transformations gave an HIV protease inhibitor intermediate. This paper is dedicated to the memory of Professor Ivar Ugi who passed away on 27th September, 2005.

Efficient enantioselective synthesis of α-hydroxy-β-amino acids using the Claisen and Curtius rearrangements

Highly enantioselective and facile synthesis of α-hydroxy-β- amino acids has been achieved using the Claisen and Curtius rearrangements as key reactions. Chiral allylic alcohols were employed, which can be prepared by asymmetric catalysis in both E- and Z

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Synthesis of the HIV-proteinase inhibitor Saquinavir: A challenge for process research

The task of process research, namely developing efficient, economically and technically as well as ecologically feasible syntheses in time, is demonstrated on the HIV-proteinase inhibitor Saquinavir (1), a complex molecule comprising six stereo-centres. Based on the first 26-step research synthesis furnishing a 10% overall yield, process research established a new, short 11-step synthesis affording a 50% overall yield.

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A Practical Synthesis of threo-3-Amino-2-hydroxycarboxylic Acids

An expeditious synthesis of (2R,3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid (2) and (2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid (4), the key components of the renin inhibitor (1) and bestatin (3), respectively, have been accomplished by featuring hi