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Updated: Sep 17, 2025

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Synthesis of C-4 indolyl 2-keto/2,3-unsaturated glycopyranosides
Chaitra Narayan Hegde1, Anil Shetty2, M G Greeshma2
1Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411 008, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India.
Abstract:
A straightforward synthesis of C-4 indolyl glycopyranosides via Michael addition of indole to easily accessible glucose-derived unsaturated ketone, catalyzed by p-TSA under mild reaction conditions, is reported. The resulting glycans are further functionalized to stable vinyl carbonates under mild reaction conditions with high yields. This approach offers a simple and scalable route to novel C-4 indolyl 2-keto/2,3-unsaturated pyranosides, having the potential to serve as versatile chiral intermediates for further functionalization in the synthesis of indole-based natural products.
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