95832-37-4

Upstream product

• 95105-20-7 (2S,3R)-3-amino-4-phenylbutane-1,2-diol 
• 503-38-8 trichloromethyl chloroformate 
• 223763-61-9 (4R,5S)-5-benzyl-4-(tert-butyldiphenylsilyloxymethyl)-1,3-oxazolidin-2-one 
• 95832-35-2 (4R,5S)-3,4-Dibenzyl-5-iodomethyl-oxazolidin-2-one 
• 95832-34-1 Benzyl-((R)-1-benzyl-allyl)-carbamic acid benzyl ester 
• 95832-31-8 Z-D-phenylalanine ethyl ester 
• 95832-30-7 N-<(benzyloxy)carbonyl>-(2R)-amino-1-phenylbut-3-ene 
• 147915-00-2 (2S,3R)-3-azido-1,2-O-methylethylidene-4-phenylbutane-1,2-diol 
• 147976-15-6 (2S,3R)-3-azido-4-phenylbutane-1,2-diol 
• 147914-98-5 (2R,3S)-1,2-O-methylethylidene-4-phenylbutane-1,2,3-triol 
• 591-51-5 phenyllithium 
• 95891-28-4 (4R,5S)-3,4-Dibenzyl-5-hydroxymethyl-oxazolidin-2-one 

Downstream Products

• 100564-98-5 (4R,5S)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acid 
• 58970-76-6 bestatin 
• 60016-66-2 benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate 
• 59554-14-2 (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid 
• 59969-65-2 (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid 
• 95832-38-5 methyl (4R,5S)-2-oxo-4-phenylmethyl-1,3-oxazolidine-5-carboxylate 
• 223763-80-2 bestatin trifluroacetate salt 
• 223763-70-0 4-benzyl-5-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 
• 223763-75-5 2-(3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid tert-butyl ester 
• 223763-56-2 (S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester 
• 223763-55-1 (4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carboxylic acid benzyl ester 
• 62023-65-8 (2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid 

Relevant academic research and scientific papers

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.

Enantiomerically pure 3-amino-2-hydroxy and 5-amino-4-hydroxy acids from D-isoascorbic acid

The chirospecific synthesis of 3-amino-2-hydroxy aldehyde or acid units is an important issue in the context of synthetic strategies directed towards the construction of biologically relevant target molecules such as amino sugars, antibiotics, enzyme inhi

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.