100992-60-7

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

• 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 
• 246506-75-2 [1-benzyl-3-cyano-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid tert-butyl ester 
• 18942-49-9 Boc-D-Phe-OH 

Relevant academic research and scientific papers

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

A practical diastereoselective synthesis of (?)-bestatin

Diastereoselective addition of nitromethane to Boc-D-Phe-H in the presence of sodium hydride in diethyl ether/hexane containing 15-crown-5 and subsequent N,O-protection with 2,2-dimethoxypropane gave trans-oxazolidine in a diastereomeric ratio of >16:1. T

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

Application of acyl cyanophosphorane methodology to the synthesis of protease inhibitors: Poststatin, eurystatin, phebestin, probestin and bestatin

Full details are given for the syntheses of the protease inhibitors, poststatin and eurystatin by the acyl cyanophosphorane coupling procedure used for the formation of α-keto amides. We have also extended this methodology to the syntheses of the related α-hydroxy amide natural products, phebestin, probestin and bestatin. The key step in the latter synthetic sequences involved diastereomeric selectivity in the reduction of the α-keto precursor to the corresponding α-hydroxy amide by the use of zinc borohydride.

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.

Novel synthesis of (-)-bestatin from L-aspartic acid

Oxazoline-4-acetate derivative 3 that could be readily obtained from L-aspartic acid was subjected to highly stereoselective hydroxylation, and subsequent Mitsunobu inversion of the hydroxyl group led to (2S,3R)-3-amino-3-benzyl-2-hydroxybutanoic acid der

A stereospecific synthesis of (-)-bestatin from L-malic acid

A highly diastereospecific route to (-)-Bestatin from L-Malic Acid has been developed. This approach features a stereocontrolled alkylation of diethyl (S)-malate and proceeds through an oxazolidone via a Curtius Rearrangement.