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Minimal protection based glycosidation (MPG) reaction employing synergistic action of [Au]/[Ag]-catalytic system

Authors : Harsha Gouda, Bijoyananda Mishra* and Srinivas Hotha*


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Abstract

Minimal protection based glycosidations (MPG) where a minimally protected glycosyl donor is used for the synthesis of glycosides is highly rewarding over the conventional glycosidation reactions. The unique feature of this semi-classical protocol is that it not only eliminates multiple steps for the glycosyl donor synthesis but also provides higher glycosidation yields. In this article, a convenient and efficient MPG reaction under synergistic action of [Au]/[Ag]-catalytic system has been identified. Glycosyl donors are effortlessly prepared in two steps from the easily accessible unprotected sugars. Glycosidations are mild, fast and high yielding (>85%) with broad substrate scope. A systematic study of solvent and temperature effect on the anomeric selectivity has been also demonstrated.

Keyword

Glycosidation, carbonate donors, gold catalysis, glycoside, minimal protection