Glycosyl imidates, 37. Direct O‐glycosylation of compounds containing a PO(OH) moiety

Abstract

AbstractThe O‐benzylated α and β‐glucosyl trichoroacetimidates 1a–α and 1a–β afforded with the phosphinic acid derivative 2 and the phosphonic acid derivative 3 directly the corresponding O‐glucosylated products 4 and 5, resp., with inversion at the anomeric center. The corresponding O‐acetylated trichloroacetimidates 1b–α and 1b–β provided both the β‐products due to neighboring group participation. With the amidophosphoric acid derivative 6 and the trichloroacetimidate 1b–α the O‐glucosylated compound 8–β was obtained. The O‐acetylated 6‐deoxy‐L‐talopyranosyl donor 12 behaved similarly. With compound 2 the α‐phosphinate 13 was formed. Dibenzyl phosphate gave the α‐phosphate 14; subsequent debenzylation led to the 6‐deoxy‐α‐L‐talopyranosyl phosphate 15.