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 synthesis method of ubenimex

The invention discloses a method for synthesizing ubenimex. The method comprises the following steps: by taking D-Boc-phenyl alaninal as a raw material, sequentially preparing hydroxynitrile, carrying out a nitrile hydrolysis reaction, performing amino protection, performing chiral resolution on (2RS,3R)-3-tert-butoxyacylamino-2-hydroxy-4-phenylbutyric acid, and synthesizing (S)-phenyl-2-((2S,3R)-3-(tert-butoxyacylamino)-2-hydroxy-4-phenylbutyramide)-4-mevalonate, thereby synthesizing the ubenimex. According to the synthetic method disclosed by the invention, the defect that the resolving agent used in the conventional synthetic method is high in toxicity (such as strychnine) or high in price (such as alpha-phenylethylamine) is overcome, the synthetic method is simple in steps and low in cost, and use of reagents such as strychnine is avoided; and moreover, a dextro-amino compound is taken as the chiral resolution agent, the price is low, the operation is simple, the stirring and recrystallization time is shortened, and the synthetic efficiency is greatly 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.