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Synthesis, Structure, and Conformation of 2′,3′-Fused Oxathiane and Thiomorpholine Uridines

✍ Scribed by Jingbo Sun; Jinchang Wu; Hua Yang

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
177 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The syntheses of two 2′,3′‐fused bicyclic nucleoside analogues, i.e., 1‐[(4a__R__,5__R__,7__R__,7a__S__)‐hexahydro‐5‐(hydroxymethyl)‐4,4‐dioxidofuro[3,4‐b][1,4]oxathiin‐7‐yl]pyrimidine‐2,4(1__H__,3__H__)‐dione (1a) and 1‐[(4a__S__,5__R__,7__R__,7a__S__)‐hexahydro‐7‐(hydroxymethyl)‐1,1‐dioxido‐2__H__‐furo[3,4‐b][1,4]thiazin‐5‐yl]pyrimidine‐ 2,4(1__H__,3__H__)‐dione (1b), are described, the key step being an intramolecular hetero‐Michael addition. Their structures and conformations, previously solved by X‐ray crystallography, were analyzed in more detail, using 1D‐ and 2D‐NMR as well as HR‐MS analyses.

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