Organofluorine compounds and fluorinating agents; 20:1 The nucleophilic perfiuoroalkylation of sugar aldehydes using a sonochemical barbier-type reaction

Article abstract of DOI:10.1055/s-1998-2101

A convenient synthesis of C-perfluoroalkylated carbohydrates 2a-c and 3a-c based on a sonochemical Zn-mediated reaction of the sugar aldehyde 1 with perfluoroalkyl iodides (C₄F₉I, C₆F₁₃I, C₈F₁₇I) has been developed. Stirring or reflux at 120°C gives no detectable products and hence the application of ultrasound is crucial. The obtained carbohydrate derivatives were stepwise deprotected (intermediates 6a-c) to the amphiphilic mesogenic compounds 7a-c consisting of a sugar moiety with free hydroxyl groups and a perfluoroalkyl tail directly attached to a sugar carbon. Moreover, the amphiphiles 7a-c were peracetylated to the furanose 8 and the pyranose 9, respectively.