Synthesis and conformational analysis of d-gluco-pyranosyl-(6,6′)-d-gluco-pyranuronate, a model compound for the inter-glycan 6,6′-ester linkage

Regioselective Anomeric O‐Benzyl Deprotection in Carbohydrates

“…To investigate the stability of other common hydroxyl protective groups under the anomeric debenzylation reaction conditions, we planned to synthesize a series of benzyl glycosides that possessed various orthogonal protecting groups, including benzyl ethers at the non‐anomeric position. Thus, perbenzylated hexoses like the perbenzylated D‐xylose 12 , [10] D‐glucose 14 , [14] D‐galactose 16 [15] and L‐rhamnose 18 [16] upon treatment with 10 % Pd/C, H 2 in methanol in the presence of sodium carbonate (1 equivalent) afforded the hemiacetals 13 , [17] 15 , [15] 17 [15] and 19 , [18] respectively, in excellent yield. In all the above transformations, no detectable amount of the products derived from hydrogenolysis of non‐anomeric benzyl groups was observed, (Table 2, entries 1–4).…”