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

✍ Scribed by Matthias Goebel; Heinz-Georg Nothofer; Günther Roß; Ivar Ugi

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 729 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00068-9

✦ Synopsis

A novel one-pot synthesis of a variety of O-peralkylated 5-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-arabinofuranoside and D-lyxofuranoside derivatives 10a and 10b respectively.