Synlett 2017; 28(17): 2311-2314
DOI: 10.1055/s-0036-1588507
letter
© Georg Thieme Verlag Stuttgart · New York

InBr3-Catalyzed Synthesis of Aryl 1,2-trans-Thio(seleno)glycosides

Teng Ma, Changwei Li, Haijing Liang, Zhaoyan Wang, Lan Yu*, Weihua Xue*
  • School of Pharmacy, Lanzhou University, Lanzhou, 730000, P. R. of China   Email: xuewh@lzu.edu.cn
We gratefully acknowledge financial support from the National Science Foundation of China (21402075, 51501080 and 21675070) and the Fundamental Research Funds for the Central Universities, Lanzhou University (lzujbky-2015-307, lzujbky-2016-146, and lzujbky-2017-62)
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Publication History

Received: 25 May 2017

Accepted after revision: 23 June 2017

Publication Date:
20 July 2017 (eFirst)

Abstract

InBr3 is demonstrated to be an efficient catalyst for reactions of fully acetated aldoses with aryl mercaptans or selenophenol at room temperature, rapidly furnishing the corresponding thioglycosides or selenoglycosides with exclusively 1,2-trans-stereoselectivity. This bromide is an air- and moisture-stable Lewis acid and therefore the reactions can be performed in air atmosphere making the procedure simple to perform.

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