Tetrahedron

The cycloaddition way to novel deoxy disaccharide analogs

MM Tamarez, RW Franck, A Geer

Index: Tamarez, Maria M.; Franck, Richard W.; Geer, Aloma Tetrahedron, 2003 , vol. 59, # 24 p. 4249 - 4259

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Citation Number: 15

Abstract

A novel heterocycloaddition merges 2-thiono-3-ketolactones with carbohydrate glycals to afford materials which resemble disaccharides with an O-glycosidic linkage at the anomeric center and a thioether linking both C-2 and C-2′, thus creating a third heterocyclic ring. Upon desulfurization, these novel cycloadducts afford materials which are models for 2- deoxydisaccharides. Studies with two keto lactones and seven glycals are described.