Synthesis of 8-(ω-hydroxyalkyl)-, 8-(ω-hydroxyalk-1-enyl)-, and 8-(ω-hydroxyalk-1-ynyl) adenines using the tert-butyldimethylsilyloxymethyl group, a new and versatile …

P Lang, G Magnin, G Mathis, A Burger…

Index: Lang; Magnin; Mathis; Burger; Biellmann Journal of Organic Chemistry, 2000 , vol. 65, # 23 p. 7825 - 7832

Full Text: HTML

Citation Number: 48

Abstract

The synthesis of 12 analogues of adenine substituted at C-8 by an ω-hydroxyalkyl, ω- hydroxyalk-1-enyl, or ω-hydroxyalk-1-ynyl chain of various length has been carried out in five or six steps starting from adenine. The analogues were obtained using a new protecting group of adenine, the tert-butyldimethylsilyloxymethyl group. 9-tert- Butyldimethylsilyloxymethyl-adenine is more soluble than adenine in organic solvents. It ...