Sucrose esterification under Mitsunobu conditions: evidence for the formation of 6-O-acyl-3′,6′-anhydrosucrose besides mono and diesters of fatty acids

Self‐Organizing Properties of Monosubstituted Sucrose Fatty Acid Esters: The Effects of Chain Length and Unsaturation

“…The spectroscopic data obtained was the same as that reported, whereas compounds 2 b, f, g, h, 3 d, and e were prepared according to the methods reported by Molinier et al [39] The syntheses of the remaining materials, Scheme 1. Synthesis of the saturated and unsaturated sucrose 1'-monoesters, series 1, by enzymatic methods.…”

“…[38] The 1'-monoesters, 1 a-f, were prepared by enzymatic methods, see Scheme 1, whereas the 6-monoesters, 2 a-h, and the 6'-monoesters, 3 a-e, were obtained by Mitsunobu coupling reactions, see Scheme 2. [39] These methods, though very selective, did not yield totally pure regioisomers, therefore further purification was performed by preparative HPLC. Due to migration phenomena, [40,41] other regioisomers could not be synthesised in the pure form.…”

“…[36,37,39] The isolated monoester fraction, which typically contained approximately 85 % of the 6-isomer and 15 % of the 6'-isomer, was subjected to purification using semi-preparative HPLC to give the pure 6-isomers and 6'-isomers.…”

Sucrose chemistry: Fast and Efficient Microwave-assisted Protocols for the Generation of Sucrose-Containing Monomer Libraries

“…Such a process performed on free sucrose affords 6,1',6'-triesters or 6,6'-diesters (Beraud et al, 1989;Bottle and Jenkins, 1984), establishing the reactivity of hydroxy groups as 6-OH > 6'-OH >1'-OH > secondary OH groups. Several interesting esters of sucrose, such as derivatives of fatty acids (Molinier et al, 2004) and 6-perfluoroalkanoates for biomedical uses (Abouhilale et al, 1991) have been prepared by this method. Treatment of the free sucrose with phthalimide under Mitsunobu conditions afforded derivative, in which the primary 6-OH and 6'-OH groups were replaced with phthalimide moieties, while the secondary ones at the C-3' and C-4' positions were converted into an epoxide (Amariutei et al, 1988).…”

Shape Dependence in the Formation of Condensed Phases Exhibited by Disubstituted Sucrose Esters

“…[43] The 1',6'-diesters, 1 a-d, were prepared by enzymatic methods, whereas the 6,6'-diesters 2 a-h, 3 a,b, and the 1',6-diester, 4 a, were obtained by Mitsunobu coupling reactions. [44] These methods, though very selective, do not supply totally pure regioisomers, therefore, further purification by using preparative HPLC was required. Due to the known migration phenomena, [45,46] regioisomers at the secondary positions cannot be synthesized in pure form.…”