175656-12-9

Upstream product

• 67-56-1 methanol 
• 494847-11-9 (2S,3R)-3-((S)-Hydroxy-methoxycarbonyl-methyl)-aziridine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 175656-06-1 (1R,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxa-6-aza-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester 
• 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 
• 175656-11-8 (2S,3S,4S)-2-Benzyloxycarbonylamino-4-hydroxy-3-methoxy-pentanedioic acid dimethyl ester 

Relevant academic research and scientific papers

Enantiospecific synthesis of 3,4-disubstituted glutamic acids via controlled stepwise ring-opening of 2,3-aziridino-γ-lactone

The preparation of enantiomerically pure 3,4-disubstituted glutamic acids is described starting from D-ribose. This preparation involved the use of a 2,3-aziridino-γ-lactone whose reactivity towards nucleophiles could be efficiently controlled to allow selective functionalization at the β-position. A key step of the strategy was a titanate-mediated transesterification of a dimethyl ester into a dibenzyl analogue, allowing efficient deprotection to the free amino acid by hydrogenolysis.

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.