A high-yielding, one-pot preparation of unsymmetrical glycosyl disulfides using 1-chlorobenzotriazole as an in situ trapping/oxidizing agent
Graphical abstract
A series of glycosyl disulfides have been efficiently prepared in a one-pot reaction using 1-chlorobenzotriazole (BtCl) as the oxidant.
Section snippets
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.
References and notes (24)
- et al.
J. Org. Chem.
(1998)et al.Carbohydr. Res.
(2004)et al.Angew. Chem., Int. Ed.
(2006)et al.Nat. Protocols
(2007) - et al.
J. Am. Chem. Soc.
(1971)et al.Carbohydr. Res.
(1977)et al.Angew. Chem., Int. Ed.
(2008) - et al.
Collect. Czech. Chem. Commun.
(1965)et al.J. Org. Chem.
(2006) - et al.
Tetrahedron Lett.
(1968) - et al.
Tetrahedron Lett.
(2007) - et al.
J. Am. Chem. Soc.
(1944), L.D. Lawson, Garlic: The Science and Therapeutic Application of Allium sativum L
(1996)et al.Curr. Med. Chem. Anti-Infect. Agents
(2005)et al.BioFactors
(2006) - et al.
Bioorg. Med. Chem.
(2008) - et al.
Curr. Org. Chem.
(2006) - et al.
Tetrahedron Lett.
(2001)et al.Can. J. Chem.
(2005) - et al.
Chem. Commun.
(2001)et al.J. Org. Chem.
(2005)
Bioorg. Med. Chem.
Carbohydr. Res.
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