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Efficient synthesis of hydrophilic phosphodiester derivatives of lipophilic alcohols via the glycosyl hydrogenphosphonate method

The preparation of five peracetylated a-glycosyl-H-phosphonates and their use in the straightforward preparation of phosphodiesters derivatives of 25-hydroxycholesterol is described. Examples of the extension of this process to other lipophilic alcohols are presented.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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The first example of anomeric glycoconjugation to phthalocyanines

Preparation and characterization of peripherally glucose substituted zinc(II) phthalocyanine 6, linked via the anomeric carbon through a novel glycosidation method is reported for the first time, for which classical Pc template chemistry with the unprotected phthalonitrile 4 could be used. Phthalocyanine 6 was formed in high yield and is displaying a high solubility in water as a primary condition for a potential biological application.

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Tetrahydropyran – Wikipedia,
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Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Article, 10343-06-3, the author is Edwards, Heather D. and a compound is mentioned, 10343-06-3, 2,3,4,6-Tetra-o-acetyl-D-glucopyranose, introducing its new discovery.

Probing the limitations of the fluorous content for tag-mediated microarray formation

The synthesis of a di-perfluorohexyl tag is reported for use in a fluorous-based carbohydrate microarray. A comparative microarray study with this di-perfluorohexyl tag and a mono-perfluorooctyl and mono-perfluorohexyl tag found the increased fluorous content conducive to better spot morphology and easier washing protocols without precluding reuse of the fluorous slide.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

The Absolute Best Science Experiment for 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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Solvent-free mechanochemical synthesis of aryl glycosides

Aryl glycosides have been prepared from a range of readily available glycosyl halides by a solvent-free mechanochemical procedure employing a planetary ball mill in excellent yields. Besides being a solvent-free reaction, the procedure has been successful in eliminating the need for employing any phase-transfer catalyst in the reaction. Copyright Taylor & Francis Group, LLC.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

The important role of 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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10343-06-3, Children learn through play, and they learn more than adults might expect. Science experiments are a great way to spark their curiosity, get their minds active, and encourage them to do something that doesn¡¯t involve a screen. 10343-06-3, C14H20O10. A document type is Article, introducing its new discovery.

Upgrading pine sawdust pyrolysis oil to green biofuels by HDO over zinc-assisted Pd/C catalyst

Upgrading pyrolysis oil by hydrodeoxygenation (HDO) is a promising route for the production of advanced biofuels. The proper reaction conditions and catalysts are important for the success of this process. Previously our research group investigated the ratio of Zn and Pd on the synergistic effect for HDO bio-oil upgrading. This present research focuses on determining the optimal reaction conditions for HDO conversion of pyrolysis oil produced from pine sawdust. Temperatures of 150, 200 and 250C and hydrogen pressures of 1.38, 2.76 and 4.14 MPa were evaluated. Syngas, liquids and coke were the primary products evaluated. Syngas was characterized using a Gas chromatography (GC). The liquids were characterized using a Gas chromatography-mass spectrometry (GC-MS). Increasing reaction temperature resulted in increased coke yields. Treatment at 250C and 1.38 MPa resulted in the highest hydrocarbon content (6.06%). The treatment at 200C and 1.38 MPa produced the largest amounts of hydrocarbons in C6-C12 range (5.07%). The physicochemical characterizations further support the GCMS results. Syngas analysis revealed that higher hydrogen pressure leads to increased hydrogen consumption and results in more oxy-compounds conversion to hydrocarbons. The syngas analysis also supports the liquid analysis result.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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The use of the 2,4-dinitrophenyl group in sugar chemistry re-examined

The use of the tertiary base 1,4-diazabicyclo<2,2,2>octane, together with 1-fluoro-2,4-dinitrobenzene in the solvent DMF, proved to be an efficient method for the introduction of the 2,4-dinitrophenyl (DNP) group at different positions, including the anomeric centre of glucose and galactose.The introduction of the DNP ethers at the anomeric centre leads exclusively to the formation of beta-DNP ethers.The latter derivatives can be easily converted with potassium carbonate in DMF into the alpha-DNP ethers.The X-ray analysis of 2,4-dinitrophenyl-2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside is discused.The DNP group can also be used as a protective group in the synthesis of a disaccharide (i.e. 8 and as a UV probe to monitor (254 nm) and analyse (HPLC) sugar intermediates.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Archives for Chemistry Experiments of 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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Utilization of aldoses as a carbonyl source in cyclocarbonylation of enynes

Figure presented. The reaction of enynes with acetyl-masked aldoses in the presence of a rhodium(I) catalyst resulted in cyclocarbonylation, thus avoiding the direct use of carbon monoxide, to afford bicyclic cyclopentenones. In rhodium catalysis, aldoses serve as a carbon monoxide equivalent by donating their carbonyl moieties on the acyclic aldehyde form to enynes. A variety of aldoses, including d-glucose, d-mannose, d-galactose, d-xylose, and d-ribose, can be used as a carbonyl source. Using the method, a wide variety of enynes were cyclocarbonylated in 22-67% yields. An asymmetric variant also proceeded with moderate to high enantioselectivity.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

A new application about 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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Synthesis of kaempferol 3- O -(3?,6?-Di- O – E – p -coumaroyl)-beta- D -glucopyranoside, efficient glycosylation of flavonol 3-OH with glycosyl o -alkynylbenzoates as donors

Kaempferol 3-O-(3?,6?-di-O-E-p-coumaroyl)-beta-d- glucopyranoside (1), an optimal metabolite of Scots pine seedlings for protection of deep-lying tissue against damaging UV-B, represents a typical acylated flavonol 3-O-glycoside. This compound was synthesized for the first time via two approaches. The first approach, starting with kaempferol, featured formation of the flavonol 3-O-glycosidic linkage with a glycosyl bromide under conventional PTC conditions. In the second approach, 5,7,4?-tri-O-benzyl- kaempferol was readily prepared from 2?,4?,6?- trihydroxyacetophenone and p-hydroxybenzoic acid, which was coupled with a glucopyranosyl o-hexynylbenzoate under the catalysis of a gold(I) complex to provide the desired 3-O-glycoside in excellent yield. A variety of the glycosyl o-hexanylbenzoates equipped with the 2-O-benzoyl group were also proven to be highly efficient donors for construction of the flavonol 3-O-glycosidic linkages.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Carbohydrate coatings via aryldiazonium chemistry for surface biomimicry

Carbohydrates are extremely important biomolecules and their immobilization onto solid surfaces is of interest for the development of new biomimetic materials and of new methods for understanding processes in glycobiology. We have developed an efficient surface modification methodology for the functionalization of a range of materials with biologically active carbohydrates based on aryldiazonium chemistry. We describe the synthesis and characterization of carbohydrate reagents, which were subsequently employed for the one-step, solution-based modification of carbon, metals, and alloys with monosaccharides. We used a combination of spectroscopic and nanogravimetric methods to characterize the structure of the carbohydrate layers; we report an average surface coverage of 7.8 ¡Á 10-10 mol cm-2 under our experimental conditions. Concanavalin A, a mannose-binding lectin, and Peanut Agglutinin, a galactose-binding lectin, were found to bind from solution to their respective monosaccharide binding partners immobilized at the surface. This result suggests that the spontaneous chemisorption of aryldiazonium monosaccharide precursors leads to the formation of monosaccharide layers that retain the biological recognition specificity of the parent carbohydrate molecule. Finally, we carried out measurements using fluorescently labeled Bovine Serum Albumin (BSA) and found that these carbohydrate coatings reduce unspecific adsorption of this protein at carbon surfaces. These results suggest that aryldiazonium-derived carbohydrate coatings may offer a promising strategy for preventing undesirable protein accumulation onto surfaces.

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Tetrahydropyran – Wikipedia,
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Extracurricular laboratory:new discovery of 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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Chemical Modification of the N Termini of Unprotected Peptides for Semisynthesis of Modified Proteins by Utilizing a Hydrophilic Protecting Group

A simple and efficient strategy for the selective modification of the peptide N terminus with an unnatural amino acid is described. A peptide having a SUMO-HisTag-TEV sequence (SUMO: small ubiquitin-related modifier, TEV: tobacco etch virus) preceding the N terminus of the target peptide was designed. Recombinant expression in E. coli and subsequent SUMO protease cleavage yielded the HisTag-TEV-target peptide. Partial protection of the lysine side chains of this peptide with d-glucopyranosyloxycarbonyl and removal of the HisTag-TEV sequence by TEV protease yielded the partially protected peptide with a free N-terminal amine. Coupling of selenocysteine selectively at the N terminus and subsequent acidic deprotection of the carbohydrate protecting groups yielded a modified peptide that can be used for native chemical ligation (NCL). As a proof of concept, the modification of a longer recombinant peptide with selenocysteinylserine (GalNAc) at the N terminus was demonstrated.

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Tetrahydropyran – Wikipedia,
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