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Polymethylhydrosiloxane (PMHS): A Convenient Option for Synthetic Applications of the Iodine/Silane Combined Reagent – Straightforward Entries to 2-Hydroxyglycals and Useful Building-Blocks of Glucuronic Acid and Glucosamine

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  • Dedicated to the memory of Professor Ernesto Fattorusso

Abstract

Polymethylhydrosiloxane (PMHS) proved to be a practically convenient alternative to triethylsilane in a large set of synthetic elaborations entailing the quick generation of glycosyl iodides with a iodine/silane combined reagent. In addition, the scope of this combined reagent was expanded to the especially fast generation of 2-acetoxyglycals, and the rapid synthesis of useful building-blocks of D-glucuronic acids and D-glucosamine. All the synthetic targets were obtained in especially short times either via one-pot procedures or through experimental sequences devoid of laborious chromatographical purifications of intermediates.

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