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Synthesis of 9-Halogenated 9-Deazaguanine N7-(2′-Deoxyribonucleosides)

✍ Scribed by Frank Seela; Khalil I. Shaikh; Thomas Wiglenda; Peter Leonard

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

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✦ Synopsis

Abstract

The syntheses of N^7^‐glycosylated 9‐deazaguanine 1a as well as of its 9‐bromo and 9‐iodo derivatives 1b,c are described. The regioselective 9‐halogenation with N‐bromosuccinimide (NBS) and N‐iodosuccinimide (NIS) was accomplished at the protected nucleobase 4a (2‐{[(dimethylamino)methylidene]amino}‐3,5‐dihydro‐3‐[(pivaloyloxy)methyl]‐4__H__‐pyrrolo[3,2‐d]pyrimidin‐4‐one). Nucleobase‐anion glycosylation of 4a–c with 2‐deoxy‐3,5‐di‐O‐(p‐toluoyl)‐α‐D‐erythro‐pentofuranosyl chloride (5) furnished the fully protected intermediates 6a–c (Scheme 2). They were deprotected with 0.01M NaOMe yielding the sugar‐deprotected derivatives 8a–c (Scheme 3). At higher concentrations (0.1M NaOMe), also the pivaloyloxymethyl group was removed to give 7a–c, while conc. aq. NH~3~ solution furnished the nucleosides 1a–c. In D~2~O, the sugar conformation was always biased towards S (67–61%).

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