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Highly Diastereoselective Oxidation of 2-Amino-2-deoxy-1-thio-β-d-glucopyranosides:  Synthesis of Imino Sulfinylglycosides

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journal contribution
posted on 25.01.2003, 00:00 by Noureddine Khiar, Inmaculada Fernández, Cristina S. Araújo, José-Antonio Rodríguez, Belén Suárez, Eleuterio Álvarez
A synthetic route to imino thioglycosides and to imino sulfinylglycosides has been developed. A detailed study on the diastereoselective oxidation of 2-amino-2-deoxy-1-thio-β-d-glucopyranosides is reported. It has been shown that the stereochemical outcome of the oxidation is highly dependent on the protective group of the amine function. While the oxidation of iminothioglycosides is slightly diastereoselective (up to 30% de in favor of the RS sulfoxide), a single isomer is obtained in the case of tetrachlorophthalimido derivatives. The absolute configuration of the sulfinyl glycoside was ascertained by NMR analysis using our recent model on the basis of the exo-anomeric effect corroborated by X-ray crystallography.