132880-34-3Relevant academic research and scientific papers
Chemical and enzymatic diastereoselective cleavage of β-D galactopyranosylsulfoxides
Khiar, Noureddine,Alonso, Ines,Rodriguez, Natividad,Fernandez-Mayoralas, Alfonso,Jimenez-Barbero, Jesus,Nieto, Ofelia,Cano, Felix,Foces-Foces, Concepcion,Martin-Lomas, Manuel
, p. 8267 - 8270 (1997)
The self induced diastereoselective oxidation of several thio-β-D- galactopyranosides to the corresponding sulfoxides, has been shown to occur in high yield. Up to 74% diastereomeric excess could be obtained depending on the structure and the conformation of the starting thioglycoside. Rs and Ss Phenylsulfinyl-β-D-galactopyranosides have been obtained in optically pure forms, their chemical as well as enzymatic hydrolysis with triflic acid and with β-galactosidase have been shown to proceed diastereoselectively, the structure of the sulfoxide 4'S with the S configuration at the sulfinyl sulfur has been determined by X-ray analysis.
