Organofluorine compounds and fluorinating agents; 20: The nucleophilic perfluoroalkylation of sugar aldehydes using a sonochemical Barbier-type reaction

[摘要]：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 degrees 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.

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