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Nucleic Acids Symposium Series 2003 3(1):7-8; doi:10.1093/nass/3.1.7
© 2003 by Oxford University Press
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Stereoselective synthesis of 2'-ß-carbon-substituted 2'-deoxy-4'-thioribonucleosides from 4-thiofuranoid glycal

Kazuhiro Haraguchi, Noriaki Shiina, Yuichi Yoshimura, Hisashi Shimada, Kyoko Hashimoto and Hiromichi Tanaka

School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan

The 4-thiofuranoid glycal 6 was converted into 1-chlorinated derivative 7 through LDA lithiation. When 7 was treated with LTMP, successful C-2 lithiation occurred, and subsequent treatment of the lithiated species with MeI gave 8. Dechlorination of 8 with Na/liq.NH3 yielded the 2-methyl glycal 9. Glycosidation of 9 with silylated thymine was mediated with PhSeCl as an electrophile, and gave the ß-isomer 10 stereoselectively. Removal of the 2'-phenylselenenyl group of 10 was effected with tributyltin radical, and subsequent deprotection furnished the target 2'-ß-methyl 4'-thiothymidine (11). In a similar manner, the corresponding cytosine analogue 12 could also be synthesized.


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