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Synthesis of 1′-Homo-N-nucleosides from Hexitols

✍ Scribed by Raffaele Saladino; Umberto Ciambecchini; Stephen Hanessian

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
118 KB
Volume
2003
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

This paper describes a new route for the synthesis of N‐(1′‐homo‐L‐gulitol)nucleosides and amino sugar analogues of N‐(1′‐homo‐L‐gulitol)nucleosides by nucleophilic epoxide ring‐opening followed by O‐heterocyclization of 1,2:5,6‐dianhydro‐3,4‐di‐O‐benzyl‐D‐mannitol and 1,2:5,6‐dianhydro‐3,4‐diazido‐D‐iditol, respectively. Magnesium perchlorate [Mg(ClO~4~)~2~] was found to be the best catalyst for the reaction of silylated bases, derived from uracil, thymine and adenine, with these bis(epoxides). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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