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Stereoselective synthesis of sugar-fused C-aryl-carbasugar derivatives from sugar-derived terminally unsubstituted dienes and Baylis-Hillman product-derived trisubstituted olefins via Diels-Alder reaction

Authors : Kadigachalam Parasuraman a,b, Sateesh Dubbu a, Ande Chennaiah a, A. K. Ibrahim Sheriff b and Yashwant D. Vankar *a


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Abstract

Sugar-fused C-aryl-carbasugar derivatives were synthesized in a stereoselective manner via Diels-Alder reaction between galactal- and glucal-derived terminally unsubstituted dienes and Baylis-Hillman product-derived trisubstituted olefins. This reaction is compatible with a variety of Baylis-Hillman product-derived trisubstituted olefins to give the corresponding sugar fused- C-aryl carbasugar derivatives with excellent regio- and stereoselectivity in good to excellent yields. Some of the products were converted into more functionalized scaffolds of wider utility and of possible biological importance.

Keyword

Carbohydrates, fused-sugars, C-aryl-carbasugar derivatives, Diels-Alder reaction, Baylis-Hillman product