102935-47-7

Upstream product

• 111-87-5 octanol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 200860-28-2 Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-phenylcarbamoyloxy-tetrahydro-pyran-4-yl ester 
• 25878-60-8 D-galactose pentaacetate 
• 4163-60-4 β-D-galactose peracetate 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 3646-73-9 α-D-galactopyranose 
• 108-24-7 acetic anhydride 
• 159702-01-9 octyl α,β-D-galactopyranoside 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 

Downstream Products

• 102935-49-9 n-octyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

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.

Glycosidation promoted by a reusable solid superacid in supercritical carbon dioxide

Superduper: A practical and cleaner synthetic protocol for various glycosides was established by means of a recyclable solid superacid promoter in supercritical carbon dioxide (scCO2). Anomeric mixtures composed of α- and β-isomers were success

Iodine: A versatile reagent in carbohydrate chemistry III. Efficient activation of glycosyl halides in combination with DDQ1

Iodine, either alone or in combination with DDQ, has been found to serve as a very efficient reagent for the conversion of 'disarmed' glycosyl halides into simple 1,2-trans-glycosides. This reagent system represents a practical alternative to traditional

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.

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.

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.

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.

Zeolite-catalyzed Helferich-type glycosylation of long-chain alcohols. Synthesis of acetylated alkyl 1,2-trans glycopyranosides and alkyl 1,2-cis C2-hydroxy-glycopyranosides

Zeolite-catalyzed glycosylation of long-chain alcohols, using the inexpensive and readily available peracetylated β-d-gluco- and galactopyranoses as glycosyl donors under solvent free conditions, has been explored for the first time. Among the various forms (H-, Na-, Fe- and Zn) of β zeolite examined as catalysts in the reaction of 1,2,3,4,6-penta-O-acetyl-β-d-galactopyranose with cetyl alcohol, Fe-β zeolite gave the maximum yield of 63% of cetyl 2,3,4,6-tetra-O-acetyl-β-d-galactopyranoside and cetyl 3,4,6-tri-O-acetyl-α-d-galactopyranoside. Fe-β Zeolite-catalyzed glycosylation was found to be general affording the title compounds in each case in a moderate yield, but with a good stereoselectivity. The yield of synthetically valuable acetylated long-chain alkyl 1,2-cis C2-hydroxy-glycopyranosides obtained in the present single-step procedure is considerably higher than that of the previously reported multi-step method employing the Stork silicon tether approach.

Synthesis of C7-C16-alkyl glycosides: Part III - Synthesis of alkyl D-galactopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst

The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivative (galactose) with fatty alkanols is used in a synthesis of C7-C16-alkyl galactopyranosides. The process occurs under the influence of tin(IV) chloride as a Lewis acid catalyst.

Optically active cyclophane receptors for mono- and disaccharides: The role of bidentate ionic hydrogen bonding in carbohydrate recognition

A new family of optically active cyclophane receptors for the complexation of mono- and disaccharides in competitive protic solvent mixtures is described. Macrocycles (-)-(R,R,R,R)-1-4 feature preorganized binding cavities formed by four 1,1′-binaphthalene-2,2′-diyl phosphate moieties bridged in the 3,3′-positions by acetylenic or phenylacetylenic spacers. The four phosphodiester groups converge towards the binding cavity and provide efficient bidentate ionic H-bond acceptor sites (Fig. 2). Benzyloxy groups in the 7,7′-positions of the 1,1′-binaphthalene moieties ensure solubility of the nanometer-sized receptors and prevent undesirable aggregation. The construction of the macrocyclic framework of the four cyclophanes takes advantage of Pd0-catalyzed aryl-acetylene cross-coupling by the Sonogashira protocol, and oxidative acetylenic homo-coupling methodology (Schemes 2 and 8-10). Several cleft-type receptors featuring one 1,1′-binaphthalene-2,2′-diyl phosphate moiety were also prepared (Schemes 1, 6, and 7). An undesired side reaction encountered during the synthesis of the target compounds was the formation of naptho[b]furan rings from 3-ethynylnaphthalene-2-ol derivatives, proceeding via 5-endo-dig cyclization (Schemes 3-5). Computer-assisted molecular modeling indicated that the macrocycles prefer nonplanar puckered, cyclobutane-type conformations (Figs. 7 and 8). According to these calculations, receptor (-)-(R,R,R,R)-1 has, on average, a square binding site, which is complementary in size to one monosaccharide. The three other cyclophanes (-)-(R,R,R,R)-2-4 feature, on average, wider rectangular cavities, providing a good fit to one disaccharide, while being too large for the complexation of one monosaccharide. This substrate selectivity was fully confirmed in 1H-NMR binding titrations. The chiroptical properties of the cyclophanes and their nonmacrocyclic precursors were investigated by circular dichroism (CD) spectroscopy. The CD spectra of the acyclic precursors showed a large dependence from the number of 1,1′-binaphthalene moieties (Fig. 9), and those of the cyclophanes were remarkably influenced by the nature of the functional groups lining the macrocyclic cavity (Fig. 11). Profound differences were also observed between the CD spectra of linear and macrocyclic tetrakis(1,1′-binaphthalene) scaffolds, which feature very different molecular shapes (Fig. 10). In 1H-NMR binding titrations with mono- and disaccharides (Fig. 13), concentration ranges were chosen to favor 1:1 host - guest binding. This stoichiometry was experimentally established by the curve-fitting analysis of the titration data and by Job plots. The titration data demonstrate conclusively that the strength of carbohydrate recognition is enhanced with an increasing number of bidentate ionic host - guest H-bonds (Table 1) in the complex formed. As a result of the formation of these highly stable H-bonds, carbohydrate complexation in competitive protic solvent mixtures becomes more favorable. Thus, cleft-type receptors (-)-(R)-7 and (-)-(R)-38 with one phosphodiester moiety form weak 1:1 complexes only in CD3CN. In contrast, macrocycle (-)-(R,R,R,R)-1 with four phosphodiester groups undergoes stable inclusion complexation with monosaccharides in CD3CN containing 2% CD3OD. With their larger number of H-bonding sites, disaccharide substrates bind even more strongly to the four phosphodiester groups lining the cavity of (-)-(R,R,R,R)-2 and complexation becomes efficient in CD3CN containing 12% CD3OD. Finally, the introduction of two additional methyl ester residues further enhances the receptor capacity of(-)-(R,R,R,R)-3, and efficient disaccharide complexation occurs already in CD3CN containing 20% CD3OD.