Abstract
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 onfiguration at the sulfinyl sulfur has been determined by X-ray analysis.
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