Somasundaram, Devaraj ; Balasubramanian, Kalpattu K. ; Bhagavathy, Shanmugasundaram (2017) Tunable stereoselectivity in the synthesis of α- and β-aryl glycosides using 1,2-α-anhydrosugars as glycosyl donors Carbohydrate Research, 449 . pp. 95-102. ISSN 0008-6215
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Official URL: http://doi.org/10.1016/j.carres.2017.07.007
Related URL: http://dx.doi.org/10.1016/j.carres.2017.07.007
Abstract
The stereochemical course of O-glycosidation of 1,2-α-d-anhydrosugars (glycal epoxides) with phenols can be tuned by varying the metal ion of the base. While the reaction of 1,2-α-d-anhydrosugars with phenols mediated by trimethylaluminium leads exclusively to 1,2-cis-α-O-aryl glycosides, similar reaction mediated by caesium carbonate gives exclusively 1,2-trans-β-O-aryl glycosides. In contrast, reaction with phenoxides generated from Grignard reagent and calcium salts affords mixture of the anomers.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | 1,2-Anhydrosugars; Glycal epoxides; Aryl glycosides; Stereoselective;Glycosidation |
ID Code: | 128941 |
Deposited On: | 07 Nov 2022 05:34 |
Last Modified: | 07 Nov 2022 05:34 |
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