The 1-diazo-sugar (VII), prepared by base treatment of 2,5-anhydro-1-deoxy-3,4-O-isopropylidene-1-nitrosoureido-DL-ribitol (VI), underwent 1,3-dipolar addition with dimethyl acetylenedicarboxylate in nearly quantitative yield, forming dimethyl 3-(2,3-O-isopropylidene-β-DL-erythrofuranosyl)pyrazole-4,5-dicarboxylate (VIII) and providing a pathway to C-nucleosides.
E. M. Acton, K. J. Ryan and L. Goodman, J. Chem. Soc. D, 1970, 313 DOI: 10.1039/C29700000313
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