title: Synthesis of glycosylthiols and reactivity studies.
abstract: The acid-catalyzed reaction of 1,2-anhydro-3,4,6-tri-O-benzyl-α-d-glucopyranose (7) as glycosyl donor with bis-trimethylsilyl sulfide as acceptor affords the α-thiol. Hence, this sterically hindered S-nucleophile as acceptor should provide with O-glycosyl trichloroacetimidates as glycosyl donors that have nonparticipating groups at C-2, glycosylthiols with the thiol group in axial position. This was confirmed for various donors (4, 16-19) with the exception of the corresponding mannosyl donor (20). However, powerful participating groups at C-2 of the donor (23-28) governed the anomeric selectivity.
authors.affiliation: Fachbereich Chemie, Universität Konstanz, Fach 725, D-78457 Konstanz, Germany.
authors.forename: Ravindra T
authors.initials: RT
authors.lastname: Dere
authors.forename: Amit
authors.initials: A
authors.lastname: Kumar
authors.forename: Vipin
authors.initials: V
authors.lastname: Kumar
authors.forename: Xiangming
authors.initials: X
authors.lastname: Zhu
authors.forename: Richard R
authors.initials: RR
authors.lastname: Schmidt
mesh_terms: D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D013438:Sulfhydryl Compounds