212312-97-5

Upstream product

• 540-51-2 2-bromoethanol 
• 604-69-3 β-D-glucose pentaacetate 
• 125412-02-4 (2-bromoethyl)-D-glucopyranoside 
• 108-24-7 acetic anhydride 

Downstream Products

• 34044-34-3 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2-acetylsulfanyl-ethoxy)-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

Synthesis and properties of new glucocationic surfactants: Model structures for marking cationic surfactants with carbohydrates

In this work, we report the synthesis of a new series of glucocationic surfactants, a class of surfactants we introduced very recently. The preparation of the surfactants is based on the synthesis of the 2-bromoethyl-2,3,4,6-tetra- O-acetyl-β-D-glucopyranoside, whose preparation was studied in order to improve yields and stereoselectivity of this key intermediate. These glucocationic amphiphiles were prepared and studied as a model of cationic surfactants marked with a carbohydrate moiety. The use of carbohydrates as markers on cationic lipids was recently introduced to induce recognition by specific receptors, present on the surface of cell membranes. The chemicophysical characterization of these model structures can give more insight on the aggregation behavior. Conductivity and surface tension measurements were performed in order to characterize the compounds from the amphiphilic point of view. The results showed a different effect of the glucosidic moiety on the cmc value with respect to the glucopyridinium cationic surfactants. The surfactants also showed the tendency to form premicellar aggregates in solution when the hydrophobicity is raised.

Enhanced efficacy of 7-hydroxy-3-methoxycadalene via glycosylation in in vivo xenograft study

7-Hydroxy-3-methoxycadalene, isolated from Zelkova serrata Makino, was confirmed as a biologically active natural compound. In this study, the efficacy of cadalene as an anticancer agent was tested. In order to address the poor physicochemical properties of cadalene, we designed and synthesized glycosylated cadalene derivatives for improved solubility and efficient drug delivery as a potential prodrug. In vitro cell viability assays confirmed that glycosylated cadalenes were less toxic and more soluble than cadalene. In an in vivo xenograft study in mice, the oral administration of glycosylated cadalenes caused a significant reduction in tumor size.

Gas chromatographic investigation of the boron trifluoride etherate-induced formation and anomerization of glucopyranosides

Boron trifluoride etherate-induced glucosylation of methanol, 1-propanol, 2-propanol, 2-bromoethanol, and 3-bromo-2-(bromomethyl)propan-1-o1, using 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose as donor, gave the corresponding β-glucopyranosides. The α-glucosides and 1,2,3,4,6-penta-O-acetyl-α-D-glucopyranose were formed as byproducts in varying amounts, according to GLC analysis. The propensity of the different glucopyranosides to anomerize was determined in separate experiments.