Title: Synthesis and anti-HIV activity of 4'-C-ethynyl-2'-deoxy-4'-thio-nucleosides
Authors: Haraguchi, Kazuhiro
Shimada, Hisashi
Akutsu, Genta
Kimura, Keigo
Tanaka, Hiromichi
Hamasaki, Takayuki
Baba, Masanori
Gullen, Elizabeth A
Dutschman, Ginger E
Cheng, Yung-Chi
Balzarini, Jan #
Issue Date: 2009
Host Document: Nucleic acids symposium series (2004) issue:53 pages:97-8
Conference: The 6th International Symposium on Nucleic Acids Chemistry location:Takayama, Gifu, Japan date:27 September-1 October 2009
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).
ISSN: 0261-3166
Publication status: published
KU Leuven publication type: IC
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
# (joint) last author

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