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Updated: May 15, 2025

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
CAN-Mediated Synthesis of 2-Deoxy Sugars: Access to Chiral 2-Deoxy 3-Bisindolyl-C-glycosides
1Glycochemistry Laboratory, School of Physical Sciences, Jawaharlal Nehru University, New Delhi 110067, India.
Abstract:
The 2-deoxy sugars and bisindole moieties are ubiquitously found in natural products and play a crucial role in medicinal chemistry and chemical biology. Herein, we report a novel, quick, and highly effective technique that utilizes ceric ammonium nitrate (CAN) to synthesize 2-deoxy sugars from various protected glycals within 1-2 h. Additionally, we further explore the new process of transforming 2-deoxy sugars into chirally pure 2-deoxy-3-bisindolyl-C-glycosides molecular scaffolds using a catalytic amount of indium trichloride (InCl3) in good yields at room temperature. This method emphasizes inherited stereo diversity and a wide substrate scope, which enables the synthesis of various new 2-deoxy 3-bisindolyl-C-glycoside analogues, paving the way for further exploration of their application in medicinal chemistry and chemical biology.
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