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DOI: 10.1055/a-1941-3801
Zinc Acetate Catalyzed Stereoselective 1,2-trans-Glycosylation Using Glycosyl Chlorides
The research was supported by the Science and Engineering Research Board (SERB), DST New Delhi (RJF/2020/000083). T.M.B gratefully acknowledges the SERB for financial support in the form of a Ramanujan Fellowship. R.P.I acknowledges the Council of Scientific and Industrial Research (CSIR) for a Fellowship.
The IICT Communication Number: IICT/Pubs./2022/169.
Abstract
We report a strategy for the stereoselective synthesis of 1,2-trans-glycosides in the absence of neighboring group participation. The present protocol for the selective glycosylation mainly relies on catalyst control rather than protecting group selection. By using this protocol, several glycosides were prepared. Zinc acetate was found to be the optimal catalyst, providing the desired 1,2-trans-glycosides from glucose- and mannose-derived glycosyl halides at room temperature instead of low-temperature conditions.
Key words
glycosyl chloride - no neighboring group participation - 1,2-trans-glycosylation - zinc acetateSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1941-3801.
- Supporting Information
Publication History
Received: 11 August 2022
Accepted after revision: 07 September 2022
Accepted Manuscript online:
12 September 2022
Article published online:
12 October 2022
© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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