116661-86-0

Basic information

• Product Name: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID
• Synonyms: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID;N-BOC-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID;BOC-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOIC ACID;BOC-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRIC ACID;BOC-(2R,3R)-APNS-OH;(2R,3R)-3-(BOC-AMINO)-2-HYDROXY-4-PHENYLBUTYRIC ACID;N-T-boc-(2R,3R)-3-amino-2-hydroxy-4-*phenylbutyri;(2S,3S)-3-(TERT-BUTOXYCARBONYLAMINO)-2-HYDROXY-4-PHENYLBUTYRIC ACID
• CAS NO: 116661-86-0
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• Mol File: 116661-86-0.mol

Chemical Properties

• Melting Point: 147-148 °C
• Boiling Point: 499.1°Cat760mmHg
• Flash Point: 255.7°C
• Appearance: /
• Density: 1.215g/cm³
• Vapor Pressure: 8.81E-11mmHg at 25°C
• Refractive Index: 1.542
• PKA: 3.57±0.17(Predicted)
• CAS DataBase Reference: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(116661-86-0)
• EPA Substance Registry System: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(116661-86-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 116661-86-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C15H21NO5/c1-15(2,3)21-14(20)16-11(12(17)13(18)19)9-10-7-5-4-6-8-10/h4-8,11-12,17H,9H2,1-3H3,(H,16,20)(H,18,19)/t11-,12-/m0/s1

Upstream product

• 116565-03-8 N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 209173-80-8 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid 
• 290836-34-9 (3S)-1,1-dibromo-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 
• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 147915-02-4 (2S,3S)-3-amino-4-phenylbutane-1,2-diol 
• 200616-22-4 (2S,3S)-3-N,N-dibenzylamino-4-phenylbutane-1,2-diol 
• 474022-71-4 (2S,3S)-3-N,N-dibenzylamino-1-isopropoxydimethylsilyl-4-phenylbutan-2-ol 
• 3236-56-4 dipercarbonate de O,O-t-butyle 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 62023-62-5 allophenylnorstatine 
• 290836-37-2 (3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 

Downstream Products

• 145986-90-9 N-Boc-(2S,3S)-AHPA-L-Leu-tert-butyl ester 
• 1054684-42-2 ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester 
• 147318-83-0 [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 478699-59-1 Boc-Apns-Dmt-NH(o-methylbenzyl) 
• 478699-11-5 {(1S,2S)-1-Benzyl-3-[(R)-4-(2-chloro-benzylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-2-hydroxy-3-oxo-propyl}-carbamic acid tert-butyl ester 
• 177355-09-8 [(1S,2S)-1-Benzyl-3-((2S,4S)-2-tert-butylcarbamoyl-4-chloro-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 144069-71-6 [1-benzyl-3-(2-tert-butylcarbamoyl-piperidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 359691-66-0 (S)-2-{[(R)-3-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester 
• 359691-63-7 (S)-2-{[(R)-3-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-5,5-dimethyl-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester 
• 521275-21-8 carbonic acid 1-{N-benzyl-N'-[(2,6-dimethyl-phenoxy)-acetyl]-hydrazinocarbonyl}-2-tert-butoxycarbonylamino-3-phenyl-propyl ester isobutyl ester 
• 521275-20-7 acetic acid 3-[N'-benzyl-N'-(3-tert-butoxycarbonylamino-2-isobutoxycarbonyloxy-4-phenyl-butyryl)-hydrazinocarbonyl]-2-methyl-phenyl ester 
• 602319-20-0 Benzoic acid (1S,2S)-2-tert-butoxycarbonylamino-1-carboxy-3-phenyl-propyl 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 

Relevant articles and documents

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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.

Process for preparing beta -amino- alpha -hydroxy acid derivatives

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