Pyridoneimine-catalyzed anomeric aqueous oxa-Michael additions of native mono- and disaccharides

Dey, K and Jayaraman, N (2022) Pyridoneimine-catalyzed anomeric aqueous oxa-Michael additions of native mono- and disaccharides. In: Carbohydrate Research, 520 .

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Abstract

A pyridoneimine-catalyzed oxa-Michael addition of protecting groups-free, native mono- and disaccharides with Michael acceptors in aq. solution is reported. Several mono- and disaccharides are reacted with acceptors, namely, methylvinyl ketone, acrylonitrile and tert-butyl acrylate in aq. solution, the addition catalyzed by n-pentylpyridone imine. The addition occurs site-selectively at the anomeric lactol and the remaining hydroxy functionalities are un-affected. The resulting keto-glycopyranoside products are explored in aldol, allylation and oxime product formation, occurring at either α-methyl moiety or at the keto-moiety, with appropriate synthons. In another direction, the keto-glycopyranoside is functionalized further with amino acids through reductive amination in aq. methanol solution. Formation of hemiacetal anion occurs in the presence of pyridoneimine in aq. Solution, enabling subsequent addition to occur with acceptors. Facile reductive amination of the resulting keto-glycoside provides an avenue for conjugations with amino acids in the present work.

Item Type:	Journal Article
Publication:	Carbohydrate Research
Publisher:	Elsevier Ltd
Additional Information:	The copyright for this article belongs to the Elsevier Ltd.
Keywords:	Carbohydrates; Hemiacetal; Michael addition; Pyridoneimine; Reductive amination
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	10 Aug 2022 05:30
Last Modified:	10 Aug 2022 05:30
URI:	https://eprints.iisc.ac.in/id/eprint/75766

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