New strategy for the synthesis of D-glucopyranosiduronic acid glycosyl donors containing a latent C-4 acceptor

An effective synthesis of glucuronic acid glycosyl-donor and/or -acceptor was performed starting from D-glucofuranurono-6,3-lactone 1. After lactonization of benzyl glycoside 3 and regioselective protection of the 4-hydroxyl of 4 with a bulky tert -butyldiphenylsilyl group, the lactone was opened with sodium methoxide in methanol followed by benzoylation affording the fully protected methyl ester 9, in which the C-4 was differentially protected as a latent acceptor. Simple desilylation at C-4 quantitatively gave acceptor 13, while catalytic hydrogenation, followed by activation of the anomeric center, gave donor 14 and 15.