Chemical synthesis of beta-D-psicofuranosyl disaccharides.
Disaccharides composed of a beta-D-psicofuranosyl unit were prepared by the glycosylation reaction of monosaccharide acceptors including three 2,3,4,6-tetra-O-protected hexopyranoses with a D-psicofuranosyl benzyl phthalate derivative (4). A beta-D-psicofuranosidic bond was formed by the TMSOTf-promoted reaction with high selectivity. Removal of the O-protecting groups from the resulting alpha-D-hexopyranosyl beta-D-psicofuranosides furnished the first chemical synthesis of alpha-D-gluco-, alpha-D-galacto-, and alpha-D-mannopyranosyl beta-D-psicofuranosides. The common beta-D-psicofuranosyl donor 4 was derived efficiently from D-psicose in five steps.
Ueda
Atsushi
A
Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan.
Yamashita
Takanori
T
Uenishi
Jun'ichi
J
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005632:Fructose / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D004187:Disaccharides; D005663:Furans; C003243:psicose; D005632:Fructose