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-pen tenyl glycosides are efficient glycofuranosyl donors and have therefor e been used for the subsequent synthesis of various furanosyl-pyranosi de type or furanosyl-furanoside type disaccharides related to archaeba cterial glycolipids and protozoa glycoconjugates. (C) 1997 Elsevier Sc ience Ltd.