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Nucleosides XCIII. Synthesis of 6-β-d-ribofuranosyl-pyrmidines (a new class of pyrimidine c-hucleosides)

✍ Scribed by Steve Y-K. Tam; Federico G. De Las Heras; Robert S. Klein; Jack J. Fox

Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
220 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis

Recent reports have dealt with the preparation of functionalized C-glycosyl compounds 2 as synthetic intermediates for the preparation of naturally occurring C-nucleosides and their analogues 2a*d-g. As part of our general program on the synthesis of C-nucleosides, we have prepared the new C-glycosyl derivative, ethyl 3-(2,3-O-isopropylidene-5-O-trityl-@-D-ribofuranosyl)propiolate (2) 3, bearing an cz,B-acetylenic ester function at C-l of the ribose moiety. Its preparation and subsequent facile transformation into pyrazole-and triazole-C-nucleosides by means of 1,3-dipolar cycloaddition reactions are discussed in detail in a separate publication' We now report the synthesis from 3 of a new class of pyrimidine C-nucleosides in which the sugar is attached to the C-6 of the base. The synthetic routes utilize two other key intermediates,&

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