A Convenient Synthesis of Disaccharides Containing Furanoside Units.

Abstract Pent-4-enyl 2,3,5,6-tetra-O-acetyl- d -glycofuranosides were synthesized in a one-pot reaction by a ferric chloride-promoted glycosylation of 4-penten-1-ol with d -glucose, d -mannose, and d -galactose, respectively, in heterogeneous media, followed by in situ acetylation. These n -pentenyl glycosides are efficient glycofuranosyl donors and have therefore been used for the subsequent synthesis of various furanosyl-pyranoside type or furanosyl-furanoside type disaccharides related to archaebacterial glycolipids and protozoa glycoconjugates.