Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"

Tiara, Karolina; Potopnyk, Mykhaylo A.; Jarosz, Sławomir

doi:10.3762/bjoc.14.50

Cited by 3 publications

(1 citation statement)

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“…Zikopoulos and et al were synthesized different substituent sucrose by halogenated the hydroxyl groups at C −6 and C −6 ′ of sucrose and investigate their ability to inhabit dextransucrase (Zikopoulos and Nicholas, 1980). Tiara and co-worker synthesized macromolecules by the substitution of terminal positions of sucrose with different unsaturated monosac-charide units (Tiara et al, 2018). Matev and et al reported the synthesis of sucrose ester by substituted all the primary hydroxyl group with both saturated and unsaturated fatty acid chloride (C 10 -C 10 ), most of the synthesized sucrose ester showed good antibacterial and antifungal activity (Matev et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

New bio-amphiphilic structures of sucrose via amides linkages

Salman¹

2019

ijrps

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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.

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Section: Introductionmentioning

confidence: 99%