Synthesis of Ether-Linked Di- and Trisaccharide Derivatives Part II- Functionalization and Potential Applications of Ether-Linked Di- and Trisaccharides Containing d-Glucose

Abstract

W e have prepared three series of functionalized disaccharides of the type A(6->n)B and a trisaccharide with the formula A-O-B-O-C, in which A = D-glucose (or i t s derivatives) and both B and C are any of Dfructose, D-galactose, J3-glucose, xylitol and glycerol (or their derivatives). These compounds resulted from the regiospecific functionalization of either A or B and either the partial or t o t a l deprotection of either 6-C-(3-deoxy-l,2 : 5,6-di-G-isopropylidene-Dglucofuranos-3-yl) -3+alkyl-l,2i)-isopropylidene~-D-glucofuranose or its analogues of type 1 described i n part 1.1 W e also report results on surface activity and biological properties of some of the mlecules prepared.

Synthesis and surfactant properties of a new “extended” glucidoamphiphile made from D‐glucose

“…HLB values were calculated by using the following relation: First, a reference P (HLB in this case) scan was carried out at 25°C. At optimal formulation [2] and [3] where x 1 and x 2 refer to Span and Tween weight fractions in the mixture that exhibits optimal formulation characteristics.…”

“…During the past years, the carbohydrate chemistry literature has described a new range of amphiphilic compounds in which the polar head is either a hexose or an itol moiety linked to an alkyl chain (R = n-C n H 2n+1 ; n = 6-18) by an atom or functional group Z (Z = O, S, OCO) (1)(2)(3)(4)(5)(6)(7)(8)(9). These compounds were found to produce micelles and liquid crystals and to stabilize emulsions, while they exhibit a better biocompatibility (lower toxicity, higher biodegradability) than the usual nonionic surfactants such as sorbitan ester derivatives.…”

Electrospray Tandem Mass Spectrometry of a Novel Series of Amphipathic Functionalized Ether-linked Di- and Trisaccharides and Cyclic Oligosaccharides

“…Banoub. more conventional glycosidic bonds. Villa and coworkers12, 13 have previously described the synthesis of a novel series of functionalized ether-linked di-and trisaccharide substrates formed without a glycosidic function. The structures of some representative members of this novel series are shown in Fig.…”