STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM D-altro-2-HEPTULOSE PHENYLOSAZONE

Article abstract of DOI:10.1016/S0008-6215(00)86026-7

Dehydration of D-altro-2-heptulose phenylosazone with methanolic sulfuric acid afforded two 3,6-anhydro-osazone derivatives (2 and 3).Compound 3 was obtained as the preponderant isomer, with inversion at C-1 (C-3 of the starting osazone), and 2 was obtained without inversion.Refluxing of 3 with copper sulfate afforded the C-nucleoside analog, namely, 2-phenyl-4-β-D-ribofuranosyl-1,2,3-osotriazole (4).Acetylation of 4 afforded the tri-O-acetyl derivative 5.The anomeric configuration was determined by c.d. and n.m.r. spectroscopy.The mass spectra of compounds 2-5 are discussed.