Optimized synthesis of a pentafluoro-gem-diol and conversion to a CF2Br-glucopyranose through trifluoroacetate-release and halogenation

Pentafluoro-gem-diols are substrates that enable the synthesis of valuable difluoromethylene-containing organic molecules through the release of trifluoroacetate. Currently, only one synthetic strategy is available to assemble these important precursors. Herein, two new synthetic strategies to a complex pentafluoro-gem-diol are compared to the existing route, and an improved synthetic route has completed. Moreover, the first synthesis of a CF2Br-glucopyranose was finished by a tandem trifluoroacetate-release halogenation/cyclization protocol. (C) 2016 Elsevier Ltd. All rights reserved.