Synthesis of fructofuranosides: efficient glycosylation with N-phenyltrifluoroacetimidate as the leaving group.
Fructofuranosyl trifluoroacetimidate 3 was demonstrated to be an effective glycosyl donor that exhibited good alpha-selectivity and good yield in fructosylation reactions. The reaction proceeds via neighboring group participation, which was proved by the isolation of a stable allylic orthoester intermediate.
Lian
Gaoyan
G
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, PR China.
Gao
Qi
Q
Lin
Feng
F
D000081:Acetamides / Q000737:chemistry; D002236:Carbohydrate Conformation; D002851:Chromatography, High Pressure Liquid; D005463:Fluoroacetates; D005632:Fructose / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007700:Kinetics; D008958:Models, Molecular; D014269:Trifluoroacetic Acid / Q000737:chemistry
D000081:Acetamides; D005463:Fluoroacetates; D005663:Furans; D005632:Fructose; C030688:trifluoroacetamide; C030686:acetamide; D014269:Trifluoroacetic Acid