77171-41-6

Basic information

• Product Name: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID
• Synonyms: N-BOC-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYL-BUTYRIC ACID;N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID;BOC-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOIC ACID;BOC-(2R,3R)-APNS-OH;BOC-(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRIC ACID;(2R,3R)-3-(BOC-AMINO)-2-HYDROXY-4-PHENYLBUTYRIC ACID;(2R,3R)-3-(boc-Amino)-2-hydroxy-4-phenylbutricacid;Boc-(2R,3R)-AHPA,
• CAS NO: 77171-41-6
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• Mol File: 77171-41-6.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 499.1°C at 760 mmHg
• Flash Point: 255.7°C
• Appearance: /
• Density: 1.215g/cm³
• Vapor Pressure: 8.81E-11mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: ?20°C
• PKA: 3.57±0.17(Predicted)
• BRN: 8993437
• 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(77171-41-6)
• EPA Substance Registry System: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID(77171-41-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 77171-41-6(Hazardous Substances Data)

Usage

Chemical Properties

White solid

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 
• 290836-37-2 (3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone 
• 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 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 72155-45-4 Boc-L-phenylalaninal 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 

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 
• 159000-71-2 Boc-Apns-Dmt-NHtBu 
• 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 

Relevant articles and documents

A ubenimex novel synthesis process

The invention discloses a novel synthesis process of ubenimex. The synthesis process comprises the following steps: enabling a raw material, namely (2S,3R)-3-amino-2-hydroxy-4-phenyl butyric acid, to react with di-tert-butyl dicarbonate ester so as to prepare an intermediate I, wherein di-tert-butyl dicarbonate ester is added in multiple batches; reacting the intermediate I with L-leucine tert-butyl ester hydrochloride so as to obtain an intermediate II, wherein L-leucine tert-butyl ester hydrochloride is preferred and is conducive to the improvement of yield and purity of the intermediate II; and respectively removing protecting groups, namely tert-butyloxy carbonyl and tert-butyl ester, of the intermediate II in an acid-base system, wherein through the operation, the protecting groups are effectively removed by regulating pH value by virtue of the acid-base system, so that the yield and purity of the finished ubenimex are improved.

Synthesis of new (-)-bestatin-based inhibitor libraries reveals a novel binding mode in the S1 pocket of the essential malaria M1 metalloaminopeptidase

The malarial PfA-M1 metallo-aminopeptidase is considered a putative drug target. The natural product dipeptide mimetic, bestatin, is a potent inhibitor of PfA-M1. Herein we present a new, efficient, and high-yielding protocol for the synthesis of bestatin derivatives from natural and unnatural N-Boc-d-amino acids. A diverse library of bestatin derivatives was synthesized with variants at the side chain of either the α-hydroxyβ-amino acid (P1) or the adjacent naturalα-amino acid (P1′). Surprisingly, we found that extended aromatic side chains at the P1 position resulted in potent inhibition against PfA-M1. To understand these data, we determined the X-ray cocrystal structures of PfA-M1 with two derivatives having either a Tyr(OMe) 15 or Tyr(OBzl) 16 at the P1 position and observed substantial inhibitor-induced rearrangement of the primary loop within the PfA-M1 pocket that interacts with the P1 side chain. Our data provide important insights for the rational design of more potent and selective inhibitors of this enzyme that may eventually lead to new therapies for malaria.

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.