Synthesis and Immunological Evaluation of Fluorinated Α-C-galactosylceramide Analogs

A synthesis of difluorinated alpha-C-galactosylceramides analogs featuring an extra hydroxy group in 1'-position is reported. These compounds were prepared according to unprecedented and unusual methodologies that were previously reported by the authors on simpler substrates. Unfortunately, all four compounds, which feature different lipidic chain lengths, failed to activate iNKT cells. The question whether it is due to the anomeric oxygen/CF2 transposition or to the presence of the extra OH group remains unanswered. (C) 2015 Published by Elsevier B.V.