105181-72-4

Basic information

• Product Name: (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid
• Synonyms: (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid
• CAS NO: 105181-72-4
• Molecular Weight: 295.335
• Mol File: 105181-72-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 499.1±45.0 °C(Predicted)
• Density: 1?+-.0.06 g/cm3(Predicted)
• CAS DataBase Reference: (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid(105181-72-4)
• EPA Substance Registry System: (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid(105181-72-4)

Safety Data

• Hazardous Substances Data: 105181-72-4(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid" is an amino acid derivative with a tert-butoxycarbonylamino group attached to the third carbon and a hydroxy and phenyl group attached to the second and fourth carbon, respectively. Its molecular structure is characterized by a 2R,3S configuration, indicating the stereoisomeric arrangement of its constituent atoms. (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid may be utilized in various chemical reactions and synthesis processes, particularly in the field of pharmaceuticals and drug development.

Upstream product

• 3236-56-4 dipercarbonate de O,O-t-butyle 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 72155-45-4 Boc-L-phenylalaninal 
• 24424-99-5 di-tert-butyl dicarbonate 
• 209173-80-8 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid 
• 62023-62-5 allophenylnorstatine 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 290836-34-9 (3S)-1,1-dibromo-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 
• 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 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 474022-71-4 (2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol 
• 200616-22-4 (2S,3S)-3-N,N-dibenzylamino-4-phenylbutane-1,2-diol 

Downstream Products

• 144069-71-6 [1-benzyl-3-(2-tert-butylcarbamoyl-piperidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 336611-71-3 [(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 858780-97-9 ((1S,2S)-1-Benzyl-3-{(R)-5,5-dimethyl-4-[(pyridin-4-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-2-hydroxy-3-oxo-propyl)-carbamic acid tert-butyl ester 
• 858780-96-8 ((1S,2S)-1-Benzyl-3-{(R)-5,5-dimethyl-4-[(pyridin-3-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-2-hydroxy-3-oxo-propyl)-carbamic acid tert-butyl ester 
• 858780-98-0 ((1S,2S)-1-Benzyl-3-{(R)-5,5-dimethyl-4-[(pyridin-2-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-2-hydroxy-3-oxo-propyl)-carbamic acid tert-butyl ester 
• 858780-91-3 {1-benzyl-3-[5,5-dimethyl-4-(N'-methyl-N'-phenyl-hydrazinocarbonyl)-thiazolidin-3-yl]-2-hydroxy-3-oxo-propyl}-carbamic acid tert-butyl ester 
• 858780-57-1 {(1S,2S)-1-Benzyl-3-[(R)-5,5-dimethyl-4-(1-methyl-1-phenyl-ethylcarbamoyl)-thiazolidin-3-yl]-2-hydroxy-3-oxo-propyl}-carbamic acid tert-butyl ester 
• 858780-92-4 {(1S,2S)-1-Benzyl-2-hydroxy-3-[(R)-4-(2-methoxy-benzylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-3-oxo-propyl}-carbamic acid tert-butyl ester 
• 858780-93-5 {(1S,2S)-1-Benzyl-3-[(R)-4-(2-ethoxy-benzylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-2-hydroxy-3-oxo-propyl}-carbamic acid tert-butyl ester 
• 858780-94-6 {(1S,2S)-1-Benzyl-2-hydroxy-3-[(R)-4-(indan-1-ylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-3-oxo-propyl}-carbamic acid tert-butyl ester 
• 858781-01-8 3-({[(R)-3-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-5,5-dimethyl-thiazolidine-4-carbonyl]-amino}-methyl)-benzoic acid methyl ester 
• 858780-95-7 ((1S,2S)-3-{(R)-4-[(Benzo[1,3]dioxol-5-ylmethyl)-carbamoyl]-5,5-dimethyl-thiazolidin-3-yl}-1-benzyl-2-hydroxy-3-oxo-propyl)-carbamic acid tert-butyl ester 
• 858781-00-7 {(1S,2S)-1-Benzyl-3-[(R)-4-(3-carbamoyl-benzylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-2-hydroxy-3-oxo-propyl}-carbamic acid tert-butyl ester 
• 858781-02-9 {(1S,2S)-1-Benzyl-3-[(R)-4-(4-carbamoyl-benzylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-2-hydroxy-3-oxo-propyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis of di- and tripeptide analogues containing α-ketoamide as a new core structure for inhibition of HIV-1 protease

Di- and tripeptide analogues containing α-ketoamide as a new core structure and incorporating allophenylnorstatine (Apns) as a transition state mimic, were designed and synthesized in the hope of obtaining a novel structural type of HIV-1 protease inhibitors. The immediate precursor, Apns-Thz-NHBu(t) was prepared by coupling of Boc-Apns with N-tert·butyl Thz-4-carboxamide hydrochloride. Removal of Boc group followed by coupling with the respective α-ketoacid residue (P2) gave the desired dipeptides (8-12) in almost quantitative yields. The α-keto tripeptides (18-21) were obtained by oxidation of the hydroxyl group of Apns (PI) in the appropriate tripeptide, iQOA-Val-Apns-(un)substituted Thz(Oxa)-NHBu1 with DMSO/DCC. Preliminary evaluation of the activity of the synthesized derivatives was determined as percentage of enzyme inhibition at 5 μM and 50 nM levels of the di- and tripeptides respectively. The α-ketoamides displayed a significant enhanced potency relative to their parent isosteres as inhibitors of HIV-1 protease and are shown to be a promising new core structure for the development of enzyme inhibitors. A quantitative approach was attempted, using an LFE model, correlating the effect of structural modification and HIV-1 protease inhibition activity of the prepared dipeptides. The result indicates the contribution of the torsion angle by 84% to the activity of the inhibitors. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

A practical and convenient synthesis of the protease inhibitor epibestatin

A convenient synthesis of the protease inhibitor epibestatin, a useful component in protease inhibition cocktails for use in proteomics research, is described. The synthesis sequence consists of seven steps, starting from phenylacetaldehyde, yielding enantiopure epibestatin in 8% overall yield. A regioselective Mitsunobu transformation of a diol is the key step in the sequence. Georg Thieme Verlag Stuttgart.

Design and synthesis of broad-based mono- and bi- cyclic inhibitors of FIV and HIV proteases

Based on the substrate transition state and our strategy to tackle the problem of drug resistance, a series of HIV/FIV protease (HIV/FIV PR) monocyclic inhibitors incorporating a 15- or 17-membered macrocycle with an equivalent P3 or P3′ group and a uniqu