923600-35-5Relevant academic research and scientific papers
Synthesis and reactions of anhydro-azido-thio-D-lyxofuranosides
Otzen, Dirk,Voss, Juergen,Adiwidjaja, Gunadi
, p. 1249 - 1270 (2007/10/03)
2,5-anhydro-3-azido-2-thio-D-lyxofuranosides and 3,5-anhydro-2-azido-3- thio-D-lyxofuranosides were prepared from methyl D-xylofuranoside or methyl D-ribofuranoside via corresponding 2,3-epoxysugars or the 5-O-trityl derivative. The sulfur was introduced
Synthesis of optically pure 3,4-disubstituted L-glutamases from a novel 2,3-aziridino-γ-lactone 4-carboxylate derivative
Dauban,Chiaroni,Riche,Dodd
, p. 2488 - 2496 (2007/10/03)
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.
