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Updated: Feb 14, 2026
Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
L-Proline/CeCl3·7H2O-NaI mediated stereoselective synthesis of α-2-deoxy glycosides from glucal
Mukul R Gupta1, Kratima Thakur1, Naveen K Khare1
1Department of Chemistry, University of Lucknow, Lucknow, 226007, India.
Abstract:
Glucal with different alcohols can be converted into the corresponding 2-deoxy glycosides without Ferrier rearrangement in high yield by treatment with eco friendly transition metal based catalysts [CuCl3·2H2O-NaI (A) or CeCl3·7H2O-NaI (B)] and chiral amine ligand L-proline at various reaction conditions which were optimized for stereoselectivity. The catalyst CeCl3·7H2O-NaI (B) and ligand L-proline in toluene, was found to be much more efficient and high atom economic for the stereoselective glycosidation of propargyl alcohol with glucal, afforded exclusively α-2-deoxy propargyl glycoside in 98% optimized yield. The ligand L-proline was used for the first time in stereoselective glycosidation of α-2-deoxy glycosides involving glucal and alcohols.
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