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Facile preparation of C-glycosylbarbiturates and C-glycosylbarbituric acids

✍ Scribed by Martin Avalos Gonzalez; Jose L. Jimenez Requejo; Juan C. Palacios Albarran; Juan A. Gabis Perez

Publisher
Elsevier Science
Year
1986
Tongue
English
Weight
849 KB
Volume
158
Category
Article
ISSN
0008-6215

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✦ Synopsis

A general method for the synthesis of pyrimidine C-nucleosides involves a one-step reaction of aldohexoses and aldopentoses with barbituric acids. Thus, 2amino-2-deoxy-D-glucose was converted into 5-(2-amino-2-deoxy-/3D-glucopyranosyl)barbituric and 5-(2-amino-2-deoxy-B-D-glucopyranosyl)-l,3-dimethylbarbituric acids. Likewise, D-glucose, D-galactose, D-mannose, D-xylose, D-ribose, and D-arabinose were transformed into sodium 5-D-glycopyranosyl-1,3-dimethylbarbiturates (11-16; average yields of 80%). The free acids 17 and 18, with the a-D-arabinopyranosyl and /3-D-galactopyranosyl structures, were also obtained. Acetylation of 11-18 gave 0-acetylated 1,3-dimethyl-2,4,6-trioxo-lH,3H,5Hpyrimidin-5-ylidene-alditols, although some compounds with pyranoid structures were also obtained. *For a preliminary account, see ref. 1.

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