F. Seela, K. Shaikh
Jun 1, 2004
Citations
0
Influential Citations
7
Citations
Journal
Helvetica Chimica Acta
Abstract
The synthesis of the 7-halogenated derivatives 1b (7-bromo) and 1c (7-iodo) of 7-deaza-2′-deoxyxanthosine (1a) is described. A partial BrI exchange was observed when the demethylation of 6-methoxy precursor compound 4b was performed with Me3SiCl/NaI. This reaction is circumvented by the nucleophilic displacement of the MeO group under strong alkaline conditions. The halogenated 7-deaza-2′-deoxyxanthosine derivatives 1b,c show a decreased S-conformer population of the sugar moiety compared to the nonhalogenated 1a. They are expected to form stronger triplexes when they replace 1a in the 1⋅dA⋅dT base triplet.