Tetrahedron

A facile synthesis of per-O-alkylated glycono-δ-lactones from per-O-alkylated glycopyranosides and a novel ring contraction for pyranoses

M Goebel, HG Nothofer, G Roß, I Ugi

Index: Goebel, Matthias; Nothofer, Heinz-Georg; Ross, Guenther; Ugi, Ivar Tetrahedron, 1997 , vol. 53, # 9 p. 3123 - 3134

Full Text: HTML

Citation Number: 32

Abstract

A novel one-pot synthesis of a variety of O-peralkylated δ-aldonolactones 9 from their corresponding glycosides 1 is introduced. This facile procedure involves combining glycoside precursor, tin (IV) chloride and trimethylsilyl azide in methylene chloride at room temperature to furnish the title compounds in moderate to high yields. A side reaction involving extrusion of C-1 of the common carbohydrate intermediate leads to d-arabino- ...