100564-98-5

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(4R,5S)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acid is used as a chiral building block for the synthesis of biologically active molecules. Its unique structure and properties make it a valuable component in the development of new pharmaceutical agents with potential therapeutic applications.
Used in Organic Chemistry:
(4R,5S)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acid is used as a valuable building block in organic chemistry, particularly in the creation of complex molecular structures. Its reactivity and potential pharmaceutical activity make it an interesting target for further study and exploration in the field of organic synthesis.

Upstream product

• 124782-04-3 methyl (2S,3R)-3--2-hydroxy-4-phenylbutanoate 
• 95832-37-4 (4R,5S)-5-benzyl-4-(hydroxymethyl)-1,3-oxazolidin-2-one 
• 145872-15-7 (4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carboxylic acid ethyl ester 
• 223763-61-9 (4R,5S)-5-benzyl-4-(tert-butyldiphenylsilyloxymethyl)-1,3-oxazolidin-2-one 
• 591-51-5 phenyllithium 
• 147914-98-5 (2R,3S)-1,2-O-methylethylidene-4-phenylbutane-1,2,3-triol 
• 95105-20-7 (2S,3R)-3-amino-4-phenylbutane-1,2-diol 
• 147976-15-6 (2S,3R)-3-azido-4-phenylbutane-1,2-diol 
• 144676-39-1 ((R)-1-Benzyl-2-cyano-2-trimethylsilanyloxy-ethyl)-carbamic acid benzyl ester 
• 63219-70-5 N-(benzyloxycarbonyl)-D-phenylalaninal 
• 147915-00-2 (2S,3R)-3-azido-1,2-O-methylethylidene-4-phenylbutane-1,2-diol 

Downstream Products

• 95832-38-5 methyl (4R,5S)-2-oxo-4-phenylmethyl-1,3-oxazolidine-5-carboxylate 
• 145872-16-8 (S)-2-[((4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester 
• 223763-55-1 (4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carboxylic acid benzyl ester 
• 65391-42-6 Bestatin hydrochloride 
• 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 
• 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 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.