New bio-amphiphilic structures of sucrose via amides linkages

Abstract

A series of four new derivatives of sucrose have been synthesized using the straightforward methodology in order to give a mono substituted analogs of sucrose at C −6 ′ of fructose moiety. The synthesis was started from the reaction of sucrose with tert-butylchlorodiphenylsilane, which is able to react with an only less steric hindrance hydroxyl group at C −6 ′ due to its bulky structure. The other hydroxyl groups were acetylated by the reaction with acetic anhydride in pyridine. Then free the hydroxyl group at C −6 ′ again by the treatment with t-butylammonium luoride in THF. The later was activated by conversion to a good leaving group via tosylation, followed by functionalized via azidation to give the precursor of the target series hepta-O-acetyl-6'-azido-sucrose. The precursor was coupled with four alkyl halides (C 12 , C 8−4 , C 14 , C 10−8 ) via Staudinger reaction to produced the target structure after deacetylating. The purity and chemical structure of the synthesized compound was con irmed by CHN elemental analysis, high-resolution mass and 1 H, 13 C NMR spectroscopy.