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Updated: Jul 3, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Acid-Catalyzed Synthesis of C-6-Esterified Sugar Acceptors from Acetals/Ketals Using Esters as Acyl Donors
Rahul Haldar1, Sanchari Kundu1, Debaraj Mukherjee1
1Department of Chemical Sciences, Bose Institute, EN 80, Sector V, Bidhan Nagar, Kolkata, West Bengal 700091, India.
Abstract:
A H2SO4-silica/TfOH-catalyzed regioselective primary esterification of acetal/ketal-protected glycosides has been developed. 4,6-O-Benzylidene-protected glycosides reacted smoothly with esters, which served as both solvent and acylating agent, to afford C-6-esterified orthogonally protected sugar acceptors. This transformation was also effective for benzylidene-protected 2-deoxyphthalimido-d-glucosamine glycosides and hence was utilized in one-pot synthesis of disaccharide from the corresponding precursor and fucosyl donor. Selectivity was observed in the case of 2,3:5,6-di-O-isopropylidene-d-mannofuranoside and 3,4-O-isopropylidene-d-galatopyranosides affording corresponding 5- and 4-hydroxy-free derivatives as major products.
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