Studies of Hexuronic Acid Ester Glycals and the Synthesis of 2-Deoxy-β-glycoside Precursors

Abstract

Abstract The hexuronic acid methyl ester glycals with L-ribo (7), D-lyxo (9), and D-xylo configuration (11a) were synthesized and their conformations and that of the D-arabino derivative 2a were studied. Using the N-iodosuccinimide alycosylation procedure these glycals were transformed into cyclohexyl 2-deoxy-2-iodoglycosides 13 - 28 and their α/β-anomer ratios determined by 1H NMR spectrocopy. The mechanism of the N-iodosuccinimide glycosylation and the correlation between glycal conformation and glycoside configuration are discussed.