209048-63-5Relevant academic research and scientific papers
Stereoselective synthesis of the β-anomer of 4′-thionucleosides based on electrophilic glycosidation to 4-thiofuranoid glycals
Haraguchi, Kazuhiro,Takahashi, Haruhiko,Shiina, Noriaki,Horii, Chikafumi,Yoshimura, Yuichi,Nishikawa, Ayako,Sasakura, Eiko,Nakamura, Kazuo T.,Tanaka, Hiromichi
, p. 5919 - 5927 (2007/10/03)
Three types of 4-thiofuranoid glycal with different 3,5-O-silyl protecting groups were prepared and their electrophilic glycosidation was investigated. The 3,5-bis-O-(tert-butyldimethylsilyl)-4-thiofuranoid glycal (5) was obtained through mesylation of 2-deoxy-4-thio-D-erythro-pentofuranose (4) and subsequent base-promoted elimination, while thermal elimination of sulfoxide derivatives was suitable for the preparation of 3,5-O-(tetraisopropyldisiloxane-1,3-diyl) (9) and 3,5-O-(di-tert-butylsilylene) (11) 4-thioglycals. The glycosidation reactions of these 4-thioglycals were carried out, in the presence of either PhSeCl or NIS, by using silylated derivatives of uracil, thymine, cytosine, and N6-benzoyladenine. Among the three 4-thioglycals, 11 was found to be an excellent glycosyl donor, forming the desired β-anomer exclusively irrespective of the nucleobase employed.
Electrophilic addition to 4-thio furanoid glycal: A highly stereoselective entry to 2'-deoxy-44'-thio pyrimidine nucleosides
Haraguchi, Kazuhiro,Nishikawa, Ayako,Sasakura, Eiko,Tanaka, Hiromichi,Nakamura, Kazuo T.,Miyasaka, Tadashi
, p. 3713 - 3716 (2007/10/03)
4-Thio furanoid glycals with different types of O-silyl protection have been prepared from benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro- pentofuranoside. Face-selectivity for PhSeCl- or N-iodosuccimide-initiated addition of a pyrimidine base to the thioglycal protected with a 3,5-O-di-r- butylsilyl group, a highly stereoselective synthesis of β-2'-deoxy-4'-thio pyrimidine nucleoside has been accomplished.
