62023-59-0

Basic information

• Product Name: (2S,3S)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID
• Synonyms: (2S,3S)-3-(Z-AMINO)-2-HYDROXY-4-PHENYLBUTYRIC ACID;(2S,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOIC ACID;(2S,3S)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID;(2S,3S)-H-APNS-OH;Z-(2S,3S)-AHPA,
• CAS NO: 62023-59-0
• Molecular Formula: C₁₈H₁₉NO₅
• Molecular Weight: 195.22
• Mol File: 62023-59-0.mol

Chemical Properties

• Boiling Point: 581.9 °C at 760 mmHg
• Flash Point: 305.7 °C
• Appearance: /
• Density: 1.295 g/cm³
• Vapor Pressure: 2.21E-14mmHg at 25°C
• Refractive Index: 1.602
• PKA: 3.56±0.17(Predicted)
• CAS DataBase Reference: (2S,3S)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID(62023-59-0)
• EPA Substance Registry System: (2S,3S)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID(62023-59-0)

Safety Data

• Hazardous Substances Data: 62023-59-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3S)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID is used as a chiral building block for the synthesis of various pharmaceuticals and organic compounds. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which is crucial for the development of effective and safe drugs.
Used in Asymmetric Synthesis:
(2S,3S)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID is employed as a key intermediate in asymmetric synthesis, a technique used to produce enantiomerically pure compounds. Its presence in the synthesis process can help control the stereochemistry of the final product, leading to more efficient and selective reactions.
Used in Drug Development:
(2S,3S)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID has been studied for its potential roles in drug development. Its unique properties and reactivity make it a promising candidate for the design and synthesis of novel therapeutic agents with improved efficacy and selectivity.

InChI:InChI=1/C18H19NO5/c20-16(17(21)22)15(11-13-7-3-1-4-8-13)19-18(23)24-12-14-9-5-2-6-10-14/h1-10,15-16,20H,11-12H2,(H,19,23)(H,21,22)/t15-,16-/m0/s1

Upstream product

• 151-50-8 potassium cyanide 
• 501-53-1 benzyl chloroformate 
• 62023-57-8 (S)-1-(2'-benzyloxycarbonylamino-3'-phenylpropanoyl)-3,5-dimethylpyrazole 
• 62023-62-5 allophenylnorstatine 
• 126015-23-4 (2S,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 172696-23-0 (2S,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester 
• 113283-78-6 [(S)-1-((4R,6R)-4,6-Dimethyl-[1,3]dioxan-2-yl)-2-phenyl-ethyl]-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 
• 172696-22-9 (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 114744-85-3 [(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 121253-57-4 β-<<(phenylmethoxy)carbonyl>amino>-α-oxobenzenebutanoic acid ethyl ester 
• 121253-53-0 2-ethoxy-5-phenyl-4-<<(phenylmethoxy)carbonyl>amino>-3-oxo-1-pentene 
• 126061-51-6 [(1S,2S)-1-Benzyl-2-cyano-2-((1S,3S)-3-hydroxy-1-methyl-butoxy)-ethyl]-carbamic acid benzyl ester 

Downstream Products

• 62058-28-0 Z-(2S,3S)-AHPA-(S)-Leu-OBzl 
• 62058-29-1 Z-(2S,3S)-AHPA-(R)-Leu-OBzl 
• 62023-62-5 allophenylnorstatine 
• 141171-72-4 (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide 
• 172696-29-6 [(1S,2S)-1-Benzyl-3-((2S,3R,4R,5R)-3,4-dimethoxy-2,5-bis-methoxymethyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid benzyl ester 
• 863640-20-4 (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-methyl ester 
• 158221-95-5 [2-({(S)-1-[(2S,3S)-3-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-2-hydroxy-4-phenyl-butyryl]-pyrrolidine-2-carbonyl}-amino)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 128018-44-0 N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane 

Relevant articles and documents

HIV protease inhibitors

Combinatorial libraries of HIV and FIV protease inhibitors are characterized by alpha-keto amide or hydroxyethylamine core structures flanked by on one side by substituted pyrrolidines, piperidines, or azasugars and on the other side by phenylalanine, tyrosine, or substituted tyrosines. The libraries are synthesized via a one step coupling reaction. Highly efficacious drug candidates are identified by screening the libraries for binding and inhibitory activity against both HIV and FIV protease. Drug candidates displaying clinically useful activity against both HIV and FIV protease are identified as being potentially resistive against a loss of inhibitory activity due to development of resistant strains of HIV.

Selectivity in the inhibition of HIV and FIV protease: Inhibitory and mechanistic studies of pyrrolidine-containing α-keto amide and hydroxyethylamine core structures

This paper describes the development of new pyrrolidine-containing α-keto amide and hydroxyethylamine core structures as mechanism based inhibitors of the HIV and FIV proteases. It was found that the α-keto amide core structure 2 is approximately 300-fold better than the corresponding hydroxyethylamine isosteric structure and 1300-fold better than the corresponding phosphinic acid derivative as an inhibitor of the HIV protease. The α-keto amide is however not hydrated until it is bound to the HIV protease as indicated by the NMR study and the X-ray structural analysis. Further analysis of the inhibition activities of hydroxyethylamine isosteres containing modified pyrrolidine derivatives revealed that a cis-methoxy group at C-4 of the pyrrolidine would improve the binding 5- and 25-fold for the trans-isomer. When this strategy was applied to the α-keto amide isostere, a cis-benzyl ether at C-4 was found to enhance binding 3-fold. Of the core structures prepared as inhibitors of the HIV protease, none show significant inhibitory activity against the mechanistically identical FIV protease, and additional complementary groups are needed to improve inhibition.

Stereoselection in the Synthesis of threo- and erythro-3-Amino-2-hydroxy-4-phenyl-butanoic Acid using Chiral Acetal Templates

Boron trifluoride-diethyl ether mediated addition of trimethylsilylcyanide (TMSCN) to the chiral acetals derived from Z-L- and Z-D-phenyl alaninal, Z-N-benzyloxycarbonyl), and (+)-(2S,4S)- and (-)-(2R,4R)-2,4-pentanediol stereoselectivity gave the four st

Tributyltin Cyanide, a Novel Reagent for the Stereoselective Preparation of 3-Amino-2-hydroxy Acids via Cyanohydrin Intermediates

Reaction of tributyltin cyanide with optically active 2-N-benzyloxycarbonylamino aldehydes 1 gives the corresponding O-tributylstannyl cyanohydrins 2 and 3 stereoselectively.Compounds 2 and 3 are transformed in situ into the methyl 3-N-benzyloxycarbonylam