A convenient synthesis of disaccharides containing furanoside units

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.