Elsevier

Tetrahedron Letters

Volume 51, Issue 40, 6 October 2010, Pages 5309-5312
Tetrahedron Letters

A high-yielding, one-pot preparation of unsymmetrical glycosyl disulfides using 1-chlorobenzotriazole as an in situ trapping/oxidizing agent

https://doi.org/10.1016/j.tetlet.2010.07.176Get rights and content

Abstract

A high-yielding, one-pot methodology for preparing unsymmetrical glycosyl disulfides derived from sugar, alkyl/aryl or cysteine thiols is reported using 1-chlorobenzotriazole (BtCl) as the oxidant. The highlight of the method is the low temperature of coupling (−78 °C) as well as the in situ trapping of the sulfenyl intermediate, which ensures that no homodimer of R1SH (R1SSR1) is formed. The coupling efficiency is independent of sugar type, thiol position in the sugar, sugar-protecting groups, and the various products serve to illustrate the rapid synthetic access to a number of model systems in glycobiology.

Graphical abstract

A series of glycosyl disulfides have been efficiently prepared in a one-pot reaction using 1-chlorobenzotriazole (BtCl) as the oxidant.

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Acknowledgements

R.H. and M.R.C. thank the University of Cape Town, the Claude Leon Foundation and the South African National Research Foundation for a Fellowship to N.S. as well as financial support. L.Sz. thanks NKTH and OTKA (Project Nos. NK-68578 and ZA-20/2008) for the financial support in Hungary. The help of Ambati Ashok Kumar (Debrecen) with the preparation of the 4- and 6-thiosugar derivatives is acknowledged.

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