Synthesis of 4,4-difluoroglycosides using ring-closing metathesis.
4-Deoxy-4,4-difluoro-glycosides have been synthesised for the first time via a direct sequence involving ring-closing metathesis and indium-mediated difluoroallylation with 1-bromo-1,1-difluoropropene in water. Two protecting group strategies were explored, one to allow protection of the primary C-6 hydroxyl group throughout the sequence, while the second was intended to allow deprotection after RCM and before dihydroxylation. The benzyl ether could be used in the first role, and pivaloyl is effective in the second. Dihydroxylations were highly stereoselective and controlled by the orientation of the glycosidic C-O bond.
Audouard
Christophe
C
Department of Chemistry, University of Leicester, University Road, Leicester, UK.
Fawcett
John
J
Griffiths
Gerry A
GA
Percy
Jonathan M
JM
Pintat
Stéphane
S
Smith
Clive A
CA
D017611:Fluorine Compounds / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure
D017611:Fluorine Compounds; D006027:Glycosides