Efficient one-pot per-O-acetylation-thioglycosidation of native sugars, 4,6-O-arylidenation and one-pot 4,6-O-benzylidenation-acetylation of S-/O-glycosides catalyzed by Mg(OTf)2Electronic supplementary information (ESI) available. See DOI: 10.1039/c6ra23198e

• Main Authors: Mukherjee, Mana Mohan, Basu, Nabamita, Chaudhury, Aritra, Ghosh, Rina
• Format: Journal Article
• Language: English
• Published: 16.11.2016
• ISSN: 2046-2069
• DOI: 10.1039/c6ra23198e

A sequential one-pot per- O -acetylation- S -/ O -glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf) 2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6- O -arylidenation of glycosides and thioglycosides with benzaldehyde or p -methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf) 2 to produce the corresponding 4,6- O -arylidenated product in high yields. Mg(OTf) 2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield. Sequential one-pot per- O -acetylation- S -/ O -glycosidation under neat condition, regioselective 4,6- O -arylidenation and sequential one-pot benzylidenation-acetylation of Mg(OTf) 2 as non-hygroscopic, recyclable catalyst are reported.