223763-80-2

Upstream product

• 145986-90-9 N-Boc-(2S,3S)-AHPA-L-Leu-tert-butyl ester 
• 76-05-1 trifluoroacetic acid 
• 21691-53-2 L-leucine tert-butyl ester 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 72155-45-4 Boc-L-phenylalaninal 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 209173-80-8 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid 
• 191849-93-1 3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid 
• 62023-65-8 (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 186393-18-0 ((S)-1-benzyl-2-cyano-2-hydroxy-ethyl)-carbamic acid tert-butyl ester 
• 116565-03-8 N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 223763-75-5 2-(3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid tert-butyl ester 
• 100564-98-5 (4R,5S)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acid 
• 139397-07-2 (4R,5S)-4-benzyl-3-[(tert-butoxy)carbonyl]-2,2-dimethyl-1,3-oxazolidine-5-carboxylic acid 

Downstream Products

• 65391-42-6 Bestatin hydrochloride 

Relevant academic research and scientific papers

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

N-Hydroxymethyl derivatives of α-amino aldehydes used for the stereoselective syntheses of β-amino-α-hydroxy acids

The N-hydroxymethyl derivatives of α-amino aldehydes 1 were utilized for the effective synthesis of several β-amino-α-hydroxy acid derivatives in a one-pot process starting from the corresponding α-amino aldehydes. Properly protected methyl esters 3 were

Acylnitrene route to vicinal amino alcohols. Application to the synthesis of (-)-bestatin and analogues

Bestatin, valinoctin A, and microginin are naturally occurring small peptides containing a nonproteinogenic α-hydroxy-α-amino acid at the N-terminus of the peptide chain. We report here our development of a general method for the synthesis of α-hydroxy-β-amino acids and exemplify this with a synthesis of (-)-bestatin and analogues. Our synthesis utilizes an intramolecular acylnitrene-mediated aziridination to generate a key bicyclic aziridine in excellent yield and stereoselectivity. This bicyclic aziridine can be opened with a number of organometallic reagents to provide a series of substituted oxazolidinones. The oxazolidinones are readily converted to bestatin and a series of bestatin analogues. As part of this approach, we have developed a new method for the synthesis of azidoformates. We have also demonstrated that oxazolidinones can be selectively hydrolyzed in the presence of peptide bonds. This acylnitrene route to bestatin should prove useful for the synthesis of a variety of analogues of bestatin as well as other α-hydroxy-β-amino acids and their corresponding peptides.

Development of selective tight-binding inhibitors of leukotriene A4 hydrolase

Leukotriene A4 hydrolase is a zinc-containing enzyme which exhibits both epoxide hydrolase and aminopeptidase activities. Since the enzyme product leukotriene B4 is an inflammatory mediator, it is of interest to develop selective inh