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Usage

Uses

Used in Organic Synthesis:
Octyl 2,3,4,6-O-Tetraacetyl-β-D-mannopyranoside is utilized as an intermediate in organic synthesis for the preparation of various complex organic molecules and pharmaceutical compounds. Its unique structure, which includes a carbohydrate core and an extended hydrophobic chain, makes it a versatile building block for the development of new chemical entities with potential applications in medicine, materials science, and other fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Octyl 2,3,4,6-O-Tetraacetyl-β-D-mannopyranoside is used as a key component in the synthesis of glycoconjugates and other bioactive molecules. These molecules can have enhanced solubility, stability, and bioavailability, which are crucial factors for drug development. Octyl 2,3,4,6-O-Tetraacetyl-b-D-mannopyranoside's ability to form stable glycosidic linkages with other molecules makes it an important tool in the creation of new drugs and drug delivery systems.
Used in Materials Science:
Octyl 2,3,4,6-O-Tetraacetyl-β-D-mannopyranoside also finds applications in materials science, where it can be used to develop new types of polymers, coatings, and other materials with specific properties. Octyl 2,3,4,6-O-Tetraacetyl-b-D-mannopyranoside's hydrophilic and hydrophobic balance, along with its ability to form stable linkages, makes it suitable for creating materials with tailored characteristics, such as improved biocompatibility, self-healing properties, or stimuli-responsive behavior.

InChI:InChI=1/C22H36O10/c1-6-7-8-9-10-11-12-27-22-21(31-17(5)26)20(30-16(4)25)19(29-15(3)24)18(32-22)13-28-14(2)23/h18-22H,6-13H2,1-5H3/t18?,19-,20+,21-,22-/m1/s1

Upstream product

• 111-87-5 octanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 934-87-2 S-phenyl thioacetate 
• 108-24-7 acetic anhydride 
• 29836-26-8 n-octyl β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 83-87-4 D-glucose pentaacetate 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 724771-79-3 octyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside 
• 724771-77-1 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(8-iodo-octyloxy)-tetrahydro-pyran-4-yl ester 
• 2280-44-6 D-Glucose 
• 188778-83-8 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(8-hydroxy-octyloxy)-tetrahydro-pyran-4-yl ester 
• 724771-76-0 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(8-acetoxy-octyloxy)-tetrahydro-pyran-4-yl ester 
• 1464-44-4 phenyl-β-D-glucopyranoside 

Downstream Products

• 102935-48-8 octyl (2,3,4,6-tetra-O-acetyl)-α-D-glucopyranoside 
• 149342-80-3 octyl α-D-galactopyranoside 
• 102935-49-9 n-octyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 
• 6801-93-0 1-octyl-β-D-mannopyranoside 

Relevant academic research and scientific papers

Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters

Octyl β-D-glucopyranoside (OBG), prepared from D-glucose and octan-1-ol employing MW method, was subjected to direct dimolar valeroylation in pyridine at room temperature (25 °C) with valeroyl chloride. This mainly furnished the corresponding 3,6-di-O-valeroate in 57% yield indicating the regioselectivity at C-6 and C-3 positions. For structural elucidation and to get newer glucopyranosides of potential antimicrobial 3,6-di-O-valeroate was further converted into four novel 2,4-di-O-acyl esters reasonably in good yields. Per-O-acetate and per-O-benzoate of OBG were also prepared for SAR study. PASS predication and in vitro antimicrobial studies established them as better antifungal agent than that of antibacterial. SAR study along with AdmetSAR and SwissADME suggested that incorporation of alkanoyl and aromatic ester groups on octyl glucopyranoside core increase antimicrobial potentiality in very low concentration (10 μgmL?1). Molecular docking revealed that novel 2,4-di-O-tosyl ester and 2,3,4,6-tetra-O-benzoyl ester may act as competitive inhibitors of lanosterol 14-alpha demethylase.

N-Octyl (Thio)glycosides as Potential Cryoprotectants: Glass Transition Behaviour, Membrane Permeability, and Ice Recrystallization Inhibition Studies

A series of eight n-octyl (thio)glycosides (1α, β-4α, β) with d-glucose or d-galactose-configured head groups and varying anomeric configuration were synthesized and evaluated for glass transition behaviour, membrane permeability, and ice recrystallization inhibition (IRI) activity. Of these, n-octyl β-d-glucopyranoside (2β) exhibited a high glass transition temperatures (Tg), both as a neat sample and 20 wt-% aqueous solution. Membrane permeability studies of this compound revealed cellular uptake to concentrations relevant to the inhibition of intracellular ice formation, thus presenting a promising lead candidate for further biophysical and cryopreservation studies. Compounds were also evaluated as ice recrystallization inhibitors; however, no detectable activity was observed for the newly tested compounds.

Sweet surfactants: Packing parameter-invariant amphiphiles as emulsifiers and capping agents for morphology control of inorganic particles

Surfactants are not only pivotal constituents in any biological organism in the form of phospholipids, they are also essential for numerous applications benefiting from a large, internal surface, such as in detergents, for emulsification purposes, phase transfer catalysis or even nanoparticle stabilization. A particularly interesting, green class of surfactants contains glycoside head groups. Considering the variability of glycosides, a large number of surfactant isomers become accessible. According to established models in surfactant science such as the packing parameter or the hydrophilic lipophilic balance (HLB), they do not differ from each other and should, thus, have similar properties. Here, we present the preparation of a systematic set of glycoside surfactants and in particular isomers. We investigate to which extent they differ in several key features such as critical aggregation concentration, thermodynamic parameters, etc. Analytical methods like isothermal titration calorimetry (ITC), tensiometry, dynamic light scattering (DLS), small angle-X-ray scattering (SAXS), transmission electron microscopy (TEM) and others were applied. It was found that glycosurfactant isomers vary in their emulsification properties by up to two orders of magnitude. Finally, we have investigated the role of the surfactants in a microemulsion-based technique for the generation of zinc oxide (ZnO) nanoparticles. We found that the choice of the carbohydrate head has a marked effect on the shape of the formed inorganic nanocrystals.

Boronic Acids as Phase-Transfer Reagents for Fischer Glycosidations in Low-Polarity Solvents

Protocols employing phenylboronic acid as a phase-transfer reagent for Fischer glycosidations in low-polarity organic solvents are described. In addition to providing rate acceleration, the formation of a substrate-derived boronic ester alters the course of the reaction by selective promotion of a furanoside- or pyranoside-selective pathway. Computational modeling of the relative energies of the glycoside-derived boronic esters provides results that are qualitatively consistent with the observed distributions of furanoside versus pyranoside products. The boronic esters that are obtained as direct products of these reactions serve as protected intermediates for the synthesis of functionalized glycosides. Complexation of particular diol groups by the boronic acid also enables selective transformations of mixtures of carbohydrates.

Site-Selective, Copper-Mediated O-Arylation of Carbohydrate Derivatives

Site-selective functionalization of hydroxy groups in sugar derivatives is a major challenge in carbohydrate synthesis. Methods for achieving this goal will provide efficient access to new sugar-derived chemical building blocks and will facilitate the preparation or late-stage modification of complex oligosaccharides for applications in glycobiology research and drug discovery. Here, we describe site-selective, copper-promoted couplings of boronic acids with carbohydrate derivatives. These reactions generate sugar-derived aryl ethers, a structural class that is challenging to generate by other means and has not previously been accessed in a site-selective fashion. Experimental evidence and computational modeling suggest that the formation of a sugar-derived boronic ester intermediate is crucial to the selectivity of these processes, accelerating the arylation of an adjacent hydroxy group. The results demonstrate how the interactions of sugars with boron compounds can be combined with transition metal catalysis to achieve new chemical reactivity.

N-alkyl - β - D - glucopyranoside synthetic method

The invention discloses a synthesizing method of n-alkyl-beta-D-glucopyranoside. The method includes the following steps of dissolving fully-acetylated glucopyranose, n-alkyl alcohol and anhydrous stannic chloride in anhydrous methylene dichloride, stirring the mixture to have a reaction for 20 min to 70 min at the room temperature, washing the mixture through a saturated sodium carbonate solution, collecting organic phases, conducting reduced pressure distillation to obtain 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside, dissolving the 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside in methyl alcohol, adding sodium methylate to adjust the pH value to 9, having a reaction for 1.5 h at the room temperature, adjusting the pH value to be neutral through strong acid cation exchange resin, conducting filtering, steaming filtrate to obtain solvent, and drying the solvent to obtain the n-alkyl-beta-D-glucopyranoside. The n-alkyl is n-alkyl of C8-C12. The method is simple, raw materials are easy to obtain, cost is low, reaction temperature is moderate and easy to control, the method is environmentally friendly, and the prepared beta-configuration glucopyranoside is high in purity.

Synthesis and Properties of Alkyl β-d-Galactopyranoside

A series of alkyl β-d-galactopyranosides were prepared by the trichloroacetimidate method with d-galactose and alcohols with different chain lengths as raw materials. Their solubility, surface tension, emulsification, foaming, wettability, thermotropic liquid crystalline properties, and thermal stability were investigated. Alkyl β-d-galactopyranosides are soluble in water and ethanol, and the solubility decreases with increasing alkyl chain length. Decyl β-d-galactopyranoside was insoluble in water, but soluble in ethanol. Dissolution of alkyl β-d-galactopyranoside in water is an endothermic process with dissolution enthalpies greater than zero. Nonyl β-d-galactopyranoside had an excellent emulsifying?property, better foaming ability and the best foam stability. The CMC values of alkyl β-d-galactopyranosides decrease with increasing of alkyl chain length. Alkyl β-d-galactopyranosides are thermally stable up to 270?°C. Alkyl β-d-galactopyranosides show the distinctive optical texture of a thermotropic liquid crystal smectic A type phase. Decyl β-d-galactopyranoside showed the strongest wettability.

Exploring the meaning of sugar configuration in a supramolecular environment: Comparison of six octyl glycoside micelles by ITC and NMR spectroscopy

A series of octyl α- and β-glycosides of the manno- galacto- and gluco-series were synthesized and employed in formation of homo- and hetero-micelles in water. Critical micelle concentrations (cmc), thermodynamic quantities of demicellation and, to some extent, the hydrodynamic radii of glycomicelles were determined by isothermal titration calorimetry (ITC) and diffusion NMR studies. The goal of this work was to determine the significance of anomeric configuration as well as of epimerisation at the sugar ring for supramolecular features of the respective glycoside. A new projection of glycoside structures is proposed to facilitate interpretation of structure-property relationships in this regard. This journal is the Partner Organisations 2014.

Use of iodine for efficient and chemoselective glycosylation with glycosyl ortho-alkynylbenzoates as donor in presence of thioglycosides

A novel and high yielding glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors and iodine as promoter is described. The donors are stable and can be chemoselectively activated in the presence of thioethyl and thiophenyl glycosides. The application of this methodology in one-pot consecutive glycosylation reaction is described.

Solvent-free mechanochemical glycosylation in ball mill

Starting from acetobromosugars and an alcohol (alkyl/substituted alkyl/akenyl/alkynyl/glyceryl/cyclohexyl/steryl) various O-glycosides have been prepared mechanochemically under solvent-free conditions employing a planetary ball mill in the presence of metal carbonates (environmentally benign or otherwise) as promoters. The method was proven to be mild and efficient and applicable on preparative scale for the synthesis of various mono- and disaccharide glycosides. 4-Pentenyl glycoside so produced could, in four successive reactions in the same pot, be converted in high isolated yields into triazole-substituted pentyl glycoside that can find application in the area of medicinal chemistry.