175656-06-1

Upstream product

• 501-53-1 benzyl chloroformate 

Downstream Products

• 175656-08-3 (1R,2S,5S)-4-Oxo-3-oxa-6-aza-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester 
• 175656-12-9 (2S,3S,4S)-4-Benzyloxycarbonylamino-3-methoxy-5-oxo-tetrahydro-furan-2-carboxylic acid methyl ester 
• 494847-11-9 (2S,3R)-3-((S)-Hydroxy-methoxycarbonyl-methyl)-aziridine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 175656-11-8 (2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester 
• 175656-15-2 (2S,3S,4S)-3-Benzyloxy-2-benzyloxycarbonylamino-4-hydroxy-pentanedioic acid 1-benzyl ester 5-methyl ester 

Relevant academic research and scientific papers

Synthesis of optically pure 3,4-disubstituted L-glutamases from a novel 2,3-aziridino-γ-lactone 4-carboxylate derivative

The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)-methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the β,γ-positions.