New bio-amphiphilic structures of sucrose via amides linkages

  • Salih Mahdi Salman Department of Chemistry, College of Medicine, University of Diyala, Baqubah City, Diyala Governorate, Republic of Iraq

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 fluoride 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 (C12, C8-4, C14, C10-8) via Staudinger reaction to produced the target structure after deacetylating. The purity and chemical structure of the synthesized compound was confirmed by CHN elemental analysis, high-resolution mass and 1H, 13C NMR spectroscopy. 

Keywords: Staudinger reaction, Zemplen reaction, Sucrose core, silylation, biosurfactant

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Published
2019-10-16
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How to Cite
Salih Mahdi Salman. (2019). New bio-amphiphilic structures of sucrose via amides linkages. International Journal of Research in Pharmaceutical Sciences, 10(4), 3143-3154. https://doi.org/10.26452/ijrps.v10i4.1612
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Original Articles
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