✦ LIBER ✦

Facile Synthesis of 2′-Deoxyisoguanosine and Related 2′,3′-Dideoxyribonucleosides

✍ Scribed by Frank Seela; Bert Gabler

Publisher: John Wiley and Sons
Year: 1994
Tongue: German
Weight: 519 KB
Volume: 77
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19940770305

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✦ Synopsis

Abstract

The 2′‐deoxyisoguanosine (1) was synthesized by a two‐step procedure from 2′‐deoxyguanosine (5). Amination of silylated 2′‐deoxyguanosine yielded 2‐amino‐2′‐deoxyadenosine (6) which was subjected to selective deamination of the 2‐NH~2~ group resulting in compound 1. Also 2′,3′‐dideoxyisoguanosine (2) was prepared employing the photo‐substitution of the 2‐substituent of 2‐chloro‐2′,3′‐dideoxyadenosine (4). The latter was synthesized by Barton deoxygenation from 2‐chloro‐2′‐deoxyadenosine (3) or via glycosylation of 2,6‐dichloropurine (12) with the lactol 13. Compound 1 was less stable at the N‐glycosylic bond than 2′‐deoxyguanosine (5). The dideoxynucleoside 2 was deaminated by adenosine deaminase affording 2′,3′‐dideoxyxanthosine (17).

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