title: Unexpected role of O-2 "protecting" groups of glycosyl donors in mediating regioselective glycosidation.
abstract: Glycosidation of several vicinal diols reveals that exquisite regioselectivity can be achieved by using 2-O-benzoyl n-pentenyl glycoside donors and/or their cyclic 1,2-ortho ester counterparts. The regioselective preferences for both are the same, although ratios and yields may differ. In stark contrast, glycosidation of the diols with the corresponding 2-O-benzylated donors gives poor, if any, regioselectivity.
authors.affiliation: Natural Products and Glycotechnology Research Institute Inc. (NPG), 4118 Swarthmore Road, Durham, NC 27706, USA. dglucose@aol.com
authors.forename: Bert
authors.initials: B
authors.lastname: Fraser-Reid
authors.forename: J Cristobal
authors.initials: JC
authors.lastname: Lopez
authors.forename: K V
authors.initials: KV
authors.lastname: Radhakrishnan
authors.forename: Mateusz
authors.initials: M
authors.lastname: Mach
authors.forename: Urs
authors.initials: U
authors.lastname: Schlueter
authors.forename: Ana M
authors.initials: AM
authors.lastname: Gomez
authors.forename: Clara
authors.initials: C
authors.lastname: Uriel
mesh_terms: D002236:Carbohydrate Conformation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013379:Substrate Specificity
chemical_list: D006027:Glycosides