title: Synthesis of 3,6-O-(o-xylylene)glucopyranosyl fluoride, an axial-rich glycosyl donor of β-glycosylation.
abstract: Despite the reported complete β-selectivity in glycosylation with 2,4-di-O-benzyl-3,6-O-(o-xylylene)glucopyranosyl fluoride, its preparation has been inefficient. This paper describes an improved route for the donor, including the formation of the 3,6-bridge on 1,2,4-orthoacetylglucose, the preparation of which was also refined, along with a discovered feature that the 3,6-bridged glucose prefers the furanose form. Although this feature made the synthesis of the desired glucopyranosyl donor difficult, application of thermal glycosylation solved the problem. With a modifiable intermediate, the improved availability of the donor would expand the applications.
authors.affiliation: School of Science and Technology, Kwansei Gakuin University , 2-1 Gakuen, Sanda 669-1337, Japan.
authors.forename: Noriaki
authors.initials: N
authors.lastname: Asakura
authors.forename: Atsushi
authors.initials: A
authors.lastname: Motoyama
authors.forename: Takuya
authors.initials: T
authors.lastname: Uchino
authors.forename: Kotaro
authors.initials: K
authors.lastname: Tanigawa
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Yamada
mesh_terms: D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D008968:Molecular Conformation; D014992:Xylenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C586628:3,6-O-(o-xylylene)glucopyranosyl fluoride; D014992:Xylenes; D005947:Glucose