Abstract

Rajani Kuchana,¹ Sreeman K. Mamidyala,^1,2* Hari Babu Mereyalaa,^1,3*

DOI : http://dx.doi.org/10.13005/ojc/300202

The ability to selectively trap xylofuranosyloxy carbocation instead of the xylofuranosyl cation by activation of acetoxymethoxy leaving group at the anomeric centre is demonstrated for the synthesis of xylofuranosyloxymethyl nucleosides. The use of SnCl₄ as an activator gives both xylofuranosyloxymethyl and natural nucleosides, whereas use of TMSOTf exhibits selectivity to give xylofuranosyloxymethyl nucleosides in case of uracil, thymine, guanine and a mixture of nucleosides in case of cytosine and adenine.

Glycosyloxymethyl nucleosides; Lewis acid; Glycosylation; Thymine; Adenine.

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