title: Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.
abstract: Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosides. Various thioglycoside derivatives were obtained in high yields by one-pot fluoride-mediated de-silylation and thiol alkylation with alkyl halides or Michael acceptors of one common TIPS S-glycoside.
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University, POB 124, SE-22100, Lund, Sweden. ulf.nilsson@chem.lu.se.
authors.forename: S
authors.initials: S
authors.lastname: Mandal
authors.forename: U J
authors.initials: UJ
authors.lastname: Nilsson
mesh_terms: D006001:Glycoconjugates / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D006001:Glycoconjugates; D006027:Glycosides; D013438:Sulfhydryl Compounds; D013865:Thioglycosides