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Regioselective Deacetylation of Peracetylated Deoxy- C -glycopyranosides by Boron Trichloride (BCl 3 ).

A general approach for regioselective deacetylation at sugar 3-OH of peracetylated 6-deoxy- C -glucopyranosides mediated by BCl3 was developed. The approach could be extended to other sugar-derived 6-deoxy- C -glycopyranosides, such as those derived from mannose, galactose, and rhamnose, with deacetylation occurring at varied sugar hydroxyl groups, and further extended to 4-deoxy- C -glucopyranosides with deacetylation occurring at sugar 3-OH. The approach would enable access to synthetically challenging carbohydrate derivatives. A possible mechanism of the regioselectivity was proposed.

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