Exploring the Syntheses of Novel Glycomimetics. Carbohydrate Derivatives with <i>Se‐S</i> ‐ or <i>Se‐Se</i> ‐ Glycosidic Linkages

Abstract

Abstract A convenient route to Se‐S ‐glycoside derivatives was developed using glycosyl isoselenuronium salts as glycosylselenenyl transfer reagents toward thiols. Aliphatic and aromatic thiols were found to react in the presence of N,N ‐diisopropylethylamine as a base and furnished alkyl‐ or aryl glycosylselenenylsulfide derivatives. S ‐glycosylselenenyl‐cysteines were obtained similarly via reactions with O,N ‐protected cysteine. Reactions with monosaccharide thiols provided disaccharide mimics featuring Se‐S ‐ interglycosidic bonds. Further disaccharide mimics with Se‐Se interglycosidic linkage were obtained from the starting isoselenuronium salts via reactions with protected monosaccharide derivatives bearing selenol groups in 6‐ or 4‐position. The novel glycomimetics are expected to open new perspectives in biological activities and/or mechanistic studies due, i.a., to the rather uncommon Se‐S ‐ or Se‐Se bonds incorporated into a carbohydrate framework.