title: gem-Dimethyl 4-pentenyl glycosides: novel glycosylating agents and anomeric protecting groups.
abstract: Two classes of gem-dimethyl 4-n-pentenyl glycosides (i.e., C2-series and C3-series) have been prepared and studied in both the glycosylation and hydrolysis manifolds utilizing NBS as the sole stoichiometric activator. These novel glycosylating agents, which are analogues of Fraser-Reid's 4-n-pentenyl glycosyl donors, show increased reactivity in side-by-side studies by virtue of the gem-dimethyl effect.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.
authors.forename: Michael
authors.initials: M
authors.lastname: Fortin
authors.forename: Justin
authors.initials: J
authors.lastname: Kaplan
authors.forename: Khoa
authors.initials: K
authors.lastname: Pham
authors.forename: Sharon
authors.initials: S
authors.lastname: Kirk
authors.forename: Rodrigo B
authors.initials: RB
authors.lastname: Andrade
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006868:Hydrolysis; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006027:Glycosides