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A method of stereoselective synthesis of -D-thioglycosides from glucosyl-3-pyridinate donor and thiophenols/ thiols catalyzed by Co(BF4)2 was reported. The chemical structures of the target compounds were confirmed by nuclear magnetic resonance, high-resolution mass spectrometry and single crystal X-ray diffraction. The reaction has good functional group compatibility with all kinds of mercaptans and thiophenols, and can tolerate active sulfur nucleophiles including ester group, phenol/alcohol hydroxyl group, amino group and acetylamino group. It can also be used for the efficient synthesis of thioglycopeptides, which provides a new way for the rapid preparation of thioglycosides.
Hua et al. (2022) studied this question.