One-step preparation of 6-perfluoroalkylalkanoates of trehalose and sucrose for biomedical uses

Abouhilale, Samir; Greiner, Jacques; Riess, Jean G.

doi:10.1016/0008-6215(91)84045-g

Cited by 26 publications

(6 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Isolation of the 6-monoester, which is formed faster, is possible. 3,117 After 1-2 days of reaction, and evaporation of DMF, the crude residue is purified by column chromatography and the fractions are then subjected to semi-preparative HPLC to isolate the 6-O-acylsucrose, the 69-O-acylsucrose (Fig. 72), and the diester fraction, which has to be separated from the anhydrous derivatives.…”

Section: Synthesis Of Sucrose Liquid Crystalsmentioning

confidence: 99%

Thermotropic liquid crystalline glycolipids

et al. 2007

View full text Add to dashboard Cite

Are the liquid crystalline properties of the materials of living systems important in biological structures, functions, diseases and treatments? There is a growing consciousness that the observed lyotropic, and often thermotropic liquid crystallinity, of many biological materials that possess key biological functionality might be more than curious coincidence. Rather, as the survival of living systems depends on the flexibility and reformability of structures, it seems more likely that it is the combination of softness and structure of the liquid-crystalline state that determines the functionality of biological materials. The richest sources of liquid crystals derived from living systems are found in cell membranes, of these glycolipids are a particularly important class of components. In this critical review, we will examine the relationship between chemical structure and the self-assembling and self-organising properties of glycolipids that ultimately lead to mesophase formation.

show abstract

Section: Synthesis Of Sucrose Liquid Crystalsmentioning

confidence: 99%

Thermotropic liquid crystalline glycolipids

et al. 2007

View full text Add to dashboard Cite

show abstract

“…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).…”

Section: Functionalization Of Sucrose Avoiding Protecting Group Chemimentioning

confidence: 99%

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

Petrova¹,

Barros²,

Correia‐da‐Silva³

2011

Microwave Heating

View full text Add to dashboard Cite

“…[21] The reactivity of the primary hydroxy groups towards benzoyl chloride is different, the order being 6-OH Ͼ 1Ј-OH and 6Ј-OH. [ Some special techniques permit the preparation of selectively acylated sucrose derivatives in acceptable yields.…”

Section: Differentiation Of the Primary Hydroxy Groups By Esterificatmentioning

confidence: 99%