Simple synthesis of glycosylthiols and thioglycosides by rearrangement of O-glycosyl thionocarbamates

• Thionocarbamates undergo O,S-rearrangement when treated with acid.
• Glycosyl N-methyl thiolcarbamates were applied to the synthesis of heteroaryl thioglycosides.
• Both anomers of aromatic heteroaryl glycosides were prepared.
• Synthesized thioglycosides can serve as stable glycosyl acceptors.

The synthesis of thioglycosides has been achieved in a high yielding process employing thionocarbamates prepared from protected reducing sugars and N-alkyl isothiocyanate in the presence of a non-nucleophilic base (K2CO3). In the key step of the synthesis, thionocarbamates were treated with Lewis acid (TMSOTf) to give O,S-rearrangement products that were applied to the synthesis of both anomers of heteroaryl thioglycosides.

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