76739-16-7

Upstream product

• 112-92-5 1-octadecanol 
• 604-69-3 β-D-glucose pentaacetate 
• 92052-29-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 76686-61-8 ((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octadecyloxy-tetrahydro-pyran-2-yl)-methanol 
• 103328-76-3 octadecyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis and biocompatibility evaluation of fluorinated, single-tailed glucopyranoside surfactants

Partially fluorinated non-ionic surfactants are of interest for a range of biomedical applications, such as the pulmonary administration of drugs using reverse water-in-perfluorocarbon microemulsions. We herein report the synthesis and characterization of a series of partially fluorinated β-d- glucopyranoside surfactants from the respective alcohols and peracetylated β-d-glucopyranoside using BF3·Et2O as catalyst. The surfactant packing parameter of the fluorinated surfactants ranged from 0.472 to 0.534 (MOPAC calculations) or 0.562 to 0.585 (calculated from literature values), which is comparable to surfactants with a similar partially fluorinated tail. Based on an initial biocompatibility assessment, the β-d-glucopyranoside surfactants have low toxicities in the B16F10 mouse melanoma cell line and comparatively low haemolytic activities towards rabbit red blood cells. The fluorinated surfactants appear to be less toxic towards cells in culture and to have a lower haemolytic activity compared to their hydrocarbon analogs. Furthermore, an increasing degree of fluorination appears to reduce both the cytotoxicity and the haemolytic activity. Similar structure-activity relationships have been reported for other partially fluorinated surfactants. Overall, these findings suggest that the surfactants may be useful for biomedical applications, such as novel drug delivery systems. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2008.

Effects of lipid packing and intermolecular hydrogen bond on thermotropic phase transition of stearyl glucoside

The sugar anomeric effect on the thermotropic phase transition of stearyl glucoside was investigated. Standard analysis to study the phase transition through differential scanning calorimetry (DSC), and optical polarizing microscopy (OPM) was applied. In addition, small- and wide-angle X-ray scattering (SWAXS) and impedance spectroscopy (IS) were used to elucidate the phase structural information and the dielectric response of the glycolipid self-assembly system, respectively. A distinctive solid-to-liquid crystal phase transition of α- and β-stearyl glucoside was observed. At ambient temperature we observed semi-crystalline structure for the former and gel phase for the latter. α-Stearyl glucoside showed only one-step transition from semi-crystal to lamellar liquid crystal phase. In contrast, the gel phase of β-stearyl glucoside showed several distinct transition states prior to lamellar liquid crystal phase. Here the underlying reason for the observed β-stearyl glucoside polymorphism possibly involved strong intermolecular interaction originating from the combination of interlayer H-bonding and intralayer van der Waals forces.

A novel type of highly effective nonionic gemini Alkyl O-glucoside surfactants: A nersatile strategy of design

A novel type of highly effective gemini alkyl glucosides has been rationally designed and synthesized. The gemini surfactants have been readily prepared by glycosylation of the gemini alkyl chains that are synthesized with regioselective ring-opening of ethylene glycol epoxides by the alkyl alcohols. The new gemini alkyl glucosides exhibit significantly better surface activity than the known results. Then rheological, DLS, and TEM studies have revealed the intriguing self-assembly behavior of the novel gemini surfactants. This study has proved the effectiveness of the design of gemini alkyl glucosides which is modular, extendable, and synthetically simple. The new gemini surfactants have great potential as nano carriers in drug and gene delivery.

Thermotropic and lyotropic properties of long chain alkyl glycopyranosidesPart I: Monosaccharide headgroups

A systematic structure variation of a classical amphiphile (dodecyl-β-D-glucopyranoside) is performed, demonstrating the influence of anomeric linkage, configuration, ring size and flexibility as well as electric charges on the mesophase behaviour. In addition, we have investigated the thermotropic and lyotropic properties of some long chain alkyl glycosides with monosaccharide headgroups. The thermotropism was measured with polarizing microscopy and differential scanning calorimetry, and additionally the lyotropism with FTIR spectroscopy and X-ray diffraction. Copyright (C) 2000 Elsevier Science Ireland Ltd.

Thermotropic and lyotropic properties of long chain alkyl glycopyranosides. Part II. Disaccharide headgroups

We have investigated the thermotropic and lyotropic properties of some long chain alkyl glycosides with disaccharide headgroups. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method, Fourier-transform Infrared (FTIR) spectroscopy, X-ray diffraction and small angle neutron scattering. A broad thermotropic as well as lyotropic polymorphism was found. The compounds displayed thermotropic S(A) (lamellar) and cubic phases, and the investigation of the lyotropic phase behaviour led to the observation of inverted bicontinuous cubic V(II) phases, lamellar L(α) phases, normal bicontinuous cubic V(I) phases, normal columnar H(I) phases, normal discontinuous cubic I(I) phases and lyotropic cholesteric phases. The phases are discussed with respect to the chemical structures that have been varied systematically to derive structure-property relationships. (C) 2000 Elsevier Science Ireland Ltd.

SYNTHESIS OF α- AND β-GLYCOPYRANOSIDES via 1-O-ALKYLATION

1-O-Alkylation of partly protected glucopyranose 1 and galactopyranose 13 led to a convenient, short term synthesis of β-glycosides and β-disaccharides 4a-d and 14.Glucopyranose 2 with a bulky protective group at O-6 yielded exclusively the α-anomer (isomaltoside derivative) 5.