A number of C-nucleoside analogs of the D-furanose series were synthesized by using push–pull activated monosaccharide α-dimethylaminomethyleneulose (1) as a precursor. Enaminoketone 1 was reacted with o-phenylenediamine, cyanamide, and dialkyl-3-oxoglutarates to obtain benzodiazepine nucleoside analog 2, reversed C-nucleoside analog with pyrimidine ring 3, and isophthalic acid derivative 4, respectively.