100992-60-7

Basic information

• Product Name: EPIBESTATIN HYDROCHLORIDE
• Synonyms: [(2R,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL]-L-LEUCINE HYDROCHLORIDE;BESTATIN, EPI-;EPIBESTATIN;EPIBESTATIN HYDROCHLORIDE;([2r,3r]-3-amino-2-hydroxy-4-phenylbutanoyl)-l-leucine;(2R,3R)-AHPBA-Leu-OH HCl
• CAS NO: 100992-60-7
• Molecular Formula: C₁₆H₂₄N₂O₄*ClH
• Molecular Weight: 344.83
• Product Categories: inhibitor
• Mol File: 100992-60-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 620.8°Cat760mmHg
• Flash Point: 329.2°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 2.85E-16mmHg at 25°C
• Storage Temp.: −20°C
• CAS DataBase Reference: EPIBESTATIN HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: EPIBESTATIN HYDROCHLORIDE(100992-60-7)
• EPA Substance Registry System: EPIBESTATIN HYDROCHLORIDE(100992-60-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 100992-60-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H24N2O4.ClH/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11;/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22);1H/t12-,13-,14-;/m1./s1

Upstream product

• 60016-66-2 benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate 
• 2666-93-5 (S)-Leu-OMe 
• 223763-80-2 bestatin trifluroacetate salt 
• 145902-56-3 tert-Butyl (4R,5S)-4-benzyl-5-(((2S)-1-(tert-butoxy)-4-methyl-1-oxopentan-2-yl)-carbamoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 145872-15-7 (4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carboxylic acid ethyl ester 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 100564-98-5 (4R,5S)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acid 
• 247178-59-2 methyl (2S,3R)-3-(benzyloxycarbonyl)amino-2-formyloxy-4-phenylbutanoate 
• 247178-58-1 (R)-((4S,5R)-2-Benzyloxy-5-phenyl-4,5-dihydro-oxazol-4-yl)-hydroxy-acetic acid methyl ester 
• 247178-57-0 methyl (4S,5R)-2-benzyloxy-5-phenyloxazoline-4-acetate 
• 178897-35-3 (4S,5R)-4-methoxycarbonylmethyl-5-phenyloxazolidin-2-one 
• 124782-06-5 (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 59969-65-2 (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid 
• 318499-01-3 benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-tert-butyldimethylsiloxy-4-phenyl-butanoyl]-L-leucinate 

Relevant articles and documents

Synthesis of (-)-bestatin and the Taxotere side-chain via nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate

The nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate 6 with 1-nitro-2-phenylethane or with phenylnitromethane led stereoselectively to adducts 4 and 12, which where then transformed into (-)-bestatin hydrochloride and the Taxotere side-chain in over

Asymmetric Nitroaldol Reaction. Synthesis of Taxotere Side Chain and (-)-Bestatin Using (1R)-8-Phenylmenthyl Glyoxylate

The nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate (3b) with 1-nitro-1-phenylmethane (4) or with 1-nitro-2-phenylethane (13) led stereoselectively to adducts syn-2b and syn-12b, which were then transformed into the Taxotere side chain and (-)-best

A new one-pot method for the synthesis of α-siloxyamides from aldehydes or ketones and its application to the synthesis of (-)-bestatin

(equation presented) A new one-pot method for the synthesis of α-siloxyamides is described. The three substrates, H-C(CN)2O-SiMe2t-Bu, aldehydes or ketones, and primary or secondary amines, are simply mixed in one portion in acetonitrile or ether; the α-siloxyamides are obtained within short peroids in excellent yields in many cases. As a demonstration of our method, the synthesis of (-)-bestatin was carried out.