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Synthesis of 6-dimethylaminopurine 2′,3′-dideoxynucleosides

✍ Scribed by Motawia, Mohammed S. ;El-Torgoman, Abdel Moneim ;Pedersen, Erik B.

Publisher: John Wiley and Sons
Year: 1991
Tongue: English
Weight: 547 KB
Volume: 1991
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1991199101152

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✦ Synopsis

Abstract

The trimethylsilyated 6‐dimethylaminopurine 1 was coupled with the 2′,3′‐dideoxyribose derivatives 2a, b and 7 by using trimethylsilyl triflate as catalyst to yield the corresponding nucleosides 3a, b, 4a, b and 8, which were appropriately deprotected to give the desired nucleosides 5a, b and 9 as well as the related α‐isomers 6a, b and 10. The 2‐deoxyribose derivative 12 was mesylated at the 3′‐O‐position to give 13 which was coupled similarly with 1 to yield compound 14 and its α‐anomer 15. Compounds 14 and 15 were treated with tetrabutylammonium fluoride to give the desired 2′,3′‐didehydro‐2′,3′‐dideoxynucleoside analogue 16 and its α‐anomer 17.

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