SnCl2-Catalyzed Phosphorylation of Alcohols and Selective Phosphorylation/Phosphinoylation of Carbohydrates

Abstract

Phosphorylated molecules, particularly phosphorylated carbohydrates, have garnered significant interest due to their distinct biological activities, driving an urgent demand for efficient phosphorylation strategies. Herein, the successful development of a SnCl₂-catalyzed protocol for the phosphorylation of alcohols and carbohydrates is demonstrated. Notably, the reaction efficiency is found to be critically dependent on the addition order of SnCl₂ and N,N-diisopropylethylamine, a phenomenon systematically investigated through mechanistic studies. A one-pot sequential ketalization/phosphorylation strategy is established for polyol substrates, enabling streamlined access to phosphorylated derivatives. The versatility of this approach is further exemplified by achieving selective phosphorylation/phosphinoylation of carbohydrates.