209048-60-2Relevant academic research and scientific papers
STEREOSELECTIVE SYNTHESIS AND PROCESS FOR THE MANUFACTURING OF 2'-DEOXYNUCLEOSIDES
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Page/Page column 25-27, (2019/08/26)
Methods for stereoselective synthesis and manufacturing of 2'-deoxynucleosides, such as 2'-ribonucleosides, are disclosed. In some embodiments, the 2'-deoxynucleoside is a β-anomer of 2'-deoxynucleoside having a 3' a hydroxyl, 4' β hydroxymethyl configuration. Nonlimiting examples of compounds prepared by the disclosed methods include 4'-thio-2'-deoxycytidine (T-dCyd) and 5-aza-4'-thio-2'-deoxycytidine (5-aza-T-dCyd; aza-T-dCyd; aza-T-dC).
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.
