In(III) triflate-catalyzed detritylation and glycosylation by solvent-free ball milling

• A highly efficient, green method for the detritylation of trityl ethers is reported.
• Based on solvent-free grinding, it is more efficient than solution-phase reactions.
• Solvent-free glycosylation in the same pot can follow detritylation.
• Good for generating cyclotetra- to cyclooctasaccharide combinatorial libraries.

A highly efficient In(III) triflate-assisted method for the detritylation of O-trityl derivatives of carbohydrates, phenols, and alcohols using solvent-free mechanochemical method is described. In the case of carbohydrates, further reaction in the presence of an acceptor sugar leads to highly efficient glycosylation in the same pot resulting in the formation of the desired glycoside-product in very high yields. The method was applied successfully to the synthesis of a combinatorial library of galactose-based (1,6)-linked cyclohexa-, hepta-, and octasaccharides on gram scale.

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