A synthesis of the versatile C-nucleoside precursor 3, 6-anhydro-2-bromo-2-deoxy-4, 5-O-isopropylidene-7-O-trityl-D-a(Zo-heptose (lc) is described. Treatment of lc with various thiocarbamoyl-containing compounds (6) in hexamethylphosphoramide results in the formation of protected 2-substituted-5-C-ribosylthiazoles 7-9. Liberation of the nucleosides 10-12 is accomplished with either methanolic hydrogen chloride or aqueous formic acid. Complete 13C and NMR data are presented for all compounds. © 1979, American Chemical Society. All rights reserved.
