STRUCTURE AND ANOMERIC CONFIGURATION OF THE C-NUCLEOSIDE ANALOGS OBTAINED BY DEHYDRATION OF 7-DEOXY-L-manno-2-HEPTULOSE PHENYLOSAZONE

Article abstract of DOI:10.1016/S0008-6215(00)80733-8

Dehydration of 7-deoxy-L-manno-2-heptulose phenylosazone with methanolic sulfuric acid afforded two 3,6-anhydro-osazone derivatives (2 and 3).Refluxing the anhydro-osazones with copper sulfate gave two C-nucleoside analogs, namely, 4-(5-deoxy-α-L-arabinofuranosyl)-2-phenyl-$v-triazole (4) and 4-(5-deoxy-β-L-arabinofuranosyl)-2-phenyl-$v-triazole (5).The structure and anomeric configurations of 2,4, and 5 were determined by n.m.r. spectroscopy.The preponderant conformation of 4 and 5, and the mass spectra of 2,4, and 5 are discussed.