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7-Halogenated 7-Deaza-2′-deoxyxanthine 2′-Deoxyribonucleosides

✍ Scribed by Frank Seela; Khalil Shaikh

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
117 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 Br→I exchange was observed when the demethylation of 6‐methoxy precursor compound 4b was performed with Me~3~SiCl/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.

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