Efficient conversion of d-mannitol into 1,2:5,6-diacetonide with Aquivion-H as a recyclable catalyst.

Cristiano Bolchi, Rebecca Appiani, Gabriella Roda, Valentina Bertolini, Sebastiano Arnoldi, Marco Pallavicini

Carbohydrate research 2021 Jan

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Heterogeneous solid catalysis by the commercially available perfluorosulfonic ionomer Aquivion-H allowed 1,2:5,6-diacetonide of d-mannitol (1), immediate precursor of important unichiral C3-synthons, to be efficiently obtained from d-mannitol and 2,2-dimethoxypropane in DMF at room temperature. The 1,2-monoacetonide, whose intermediate formation is the rate-limiting step, could be almost completely converted into 1 with limited concurrent transformation of 1 into triacetonides. In line with recent literature reports, these results indicate that heterogeneous catalysis by Aquivion-H surpasses the performances of homogeneous acidic catalysis assuring, presumably for its peculiar morphology, a higher product selectivity. Easy recovery at the end of the reaction and recyclability are additional advantages of this solid acid catalyst. Copyright © 2021 Elsevier Ltd. All rights reserved.

Citation

Cristiano Bolchi, Rebecca Appiani, Gabriella Roda, Valentina Bertolini, Sebastiano Arnoldi, Marco Pallavicini. Efficient conversion of d-mannitol into 1,2:5,6-diacetonide with Aquivion-H as a recyclable catalyst. Carbohydrate research. 2021 Jan;499:108229