title: Synthesis and anti-HIV activity of 4'-C-ethynyl-2'-deoxy-4'-thio-nucleosides.
abstract: Synthesis of 4'-C-ethynyl-2'-deoxy-4'-thionucleosides was carried out based on electrophilic glycosidation using 4-C-ethynyl-4-thiofuranoid glycal. The glycal 15 was prepared as follows: oxidative cleavage of 6 with Pb(OAc)(4) forming the aldehyde 7, aldol reaction of 7 and subsequent silylation to furnish 8, conversion of the formyl group of 8 into an ethynyl group, and finally beta-elimination of the resulting 14 with t-BuLi. The glycosyl donor 16 was prepared by silyl-protection of 15. Electrophilic glycosidation was performed between silylated N(4)-acetylcytosine and 16 in the presence of N-iodosuccinimide. Radical-mediated removal of the introduced iodine atom followed by deprotection gave 4'-C-ethynyl-2'-deoxy-4'-thiocytidine (18).
authors.affiliation: School of Pharmaceutical Sciences, Showa University, Tokyo 142-8555, Japan.
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Haraguchi
authors.forename: Hisashi
authors.initials: H
authors.lastname: Shimada
authors.forename: Genta
authors.initials: G
authors.lastname: Akutsu
authors.forename: Keigo
authors.initials: K
authors.lastname: Kimura
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Tanaka
authors.forename: Takayuki
authors.initials: T
authors.lastname: Hamasaki
authors.forename: Masanori
authors.initials: M
authors.lastname: Baba
authors.forename: Elizabeth A
authors.initials: EA
authors.lastname: Gullen
authors.forename: Ginger E
authors.initials: GE
authors.lastname: Dutschman
authors.forename: Yung-Chi
authors.initials: YC
authors.lastname: Cheng
authors.forename: Jan
authors.initials: J
authors.lastname: Balzarini
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D019380:Anti-HIV Agents; D013872:Thionucleosides