60016-66-2

Upstream product

• 1738-69-8 L-Leucine benzyl ester 
• 59969-65-2 (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid 
• 1738-77-8 L-leucine benzyl ester p-toluenesulfonate 
• 318499-01-3 benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-tert-butyldimethylsiloxy-4-phenyl-butanoyl]-L-leucinate 
• 124782-06-5 (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 501-53-1 benzyl chloroformate 
• 178897-35-3 (4S,5R)-4-methoxycarbonylmethyl-5-phenyloxazolidin-2-one 
• 247178-57-0 methyl (4S,5R)-2-benzyloxy-5-phenyloxazoline-4-acetate 
• 247178-58-1 (R)-((4S,5R)-2-Benzyloxy-5-phenyl-4,5-dihydro-oxazol-4-yl)-hydroxy-acetic acid methyl ester 
• 247178-59-2 methyl (2S,3R)-3-(benzyloxycarbonyl)amino-2-formyloxy-4-phenylbutanoate 
• 59554-14-2 (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid 
• 95832-37-4 (4R,5S)-5-benzyl-4-(hydroxymethyl)-1,3-oxazolidin-2-one 
• 95832-38-5 methyl (4R,5S)-2-oxo-4-phenylmethyl-1,3-oxazolidine-5-carboxylate 
• 95832-30-7 N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene 

Downstream Products

• 58970-76-6 bestatin 
• 65391-42-6 Bestatin hydrochloride 
• 62023-78-3 nitrobestatin 

Relevant academic research and scientific papers

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 STEREOCONTROLLED SYNTHESIS OF (-)-BESTATIN FROM AN ACYCLIC ALLYLAMINE BY IODOCYCLOCARBAMATION

1,2-Asymmetric induction of iodocyclocarbamation is described by using allylamines 2 and 6 and the method has been succesfully applied to a stereocontrolled synthesis of bestatin.