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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 R 1SH (R 1SSR 1) 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.
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