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Nucleic Acids Symposium Series 2009 53(1):1-2; doi:10.1093/nass/nrp001
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© 2009 Oxford University Press

This article appears in the following Nucleic Acid Symposium Series issue: The 6th International Symposium on Nucleic Acids Chemistry (36th Symposium on Nucleic Acids Chemistry) [View the issue table of contents]

Reaction of the 4'-benzenesulfonyl derivatives of thymidine with organosilicon and organoaluminum reagents

Hisashi Shimada, Satoshi Kikuchi, Saori Okuda, Kazuhiro Haraguchi and Hiromichi Tanaka

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

*Corresponding author. hirotnk{at}pharm.showa-u.ac.jp

Abstract

With an aim to develop a new approach to synthesize 4'-substituted nucleosides, reactions of thymidine derivatives having a benzenesulfonyl leaving group at the 4'-position with organosilicon and organoaluminum reagents were investigated. Two substrates 4{alpha} ({alpha}-L-isomer) and 4 β (β-D-isomer) were prepared for this purpose. Although reaction of 4{alpha} with organosilicon reagents gave preferentially the 4'-substituted (allyl and N3) β-D-nucleoside, its reaction with AlMe3 gave the 4'-methyl-{alpha}-L-thymidine as the major product. On the other hand, the substrate 4β, upon reacting with AlMe3, furnished the desired 4'-methylthymidine exclusively in high yield.


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