Article

Preparation of 4'-benzenesulfonyl-3'-deoxythymidine and its reaction with organoaluminum and organosilicon reagents.

School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
Carbohydrate research (impact factor: 2.03). 09/2010; 345(18):2616-22. DOI:10.1016/j.carres.2010.09.009 pp.2616-22
Source: PubMed

ABSTRACT The 4'-benzenesulfonyl derivative of 3'-deoxythymidine was prepared from 3'-deoxythymidine-5'-aldehyde. The 4'-benzenesulfonyl leaving group undergoes a nucleophilic substitution with organoaluminum and organosilicon reagents to furnish a variety of 4'-substituted (Me, Et, i-Bu, trimethylsilylethynyl, CH(2)CH=CH(2), CN, N(3)) analogues.

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Keywords

3'-deoxythymidine-5'-aldehyde
 
4'-benzenesulfonyl
 
4'-benzenesulfonyl derivative
 
furnish
 
group undergoes
 
i-Bu
 
nucleophilic substitution
 
organosilicon reagents
 

Hisashi Shimada