29-Sep-21 News What Kind of Chemistry Facts Are We Going to Learn About 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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Anomeric O-unprotected sugars add to 3,4,6-tri-O-benzyl-2-nitro-D-galactal to accomplish nitro group-containing 1,1-linked oligosaccharides in respectable yields with good selectivities. A 1:1 mixture of toluene and n-heptane has been found as the appropriate solvent system for these Michael-type additions. The nitro group-containing 1,1-linked oligosaccharides are easily convertible into interesting trehalosamine analogues.

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9/29/21 News The Best Chemistry compound: 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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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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29-Sep-21 News Interesting scientific research on 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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A process for stereospecific preparation of glycosyl azides by reacting a metal azide with a glycosyl phosphate triester having the phosphate group cis to the adjacent C-2 substituent is disclosed.

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09/28/21 News Some scientific research about 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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A wide variety of thioglycosides 1 are selectively hydrolyzed to the corresponding 1-hydroxy sugars 2 in good yields at 0-5 deg C, by employing V2O5-H2O2 catalyzed oxidation of ammonium bromide in CH2Cl2-H2O solvent system. The methodology is very mild, environmentally benign, efficient and highly chemoselective. No side reactions such as bromination either at the anomeric position or double bond or oxidation at the sulfur are encountered.

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Sep-21 News Something interesting about 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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The invention belongs to the field of chemical synthesis and relates to synthesis of glycosyl-1-monophosphate. The method disclosed by the invention comprises the following steps of 1, performing a reaction between imidazole and phosphorus trichloride to obtain phosphite tri-imidazole, performing a reaction between the phosphite tri-imidazole and an acetylated sugar raw material of which the end position is deprotected and carrying out in-situ hydrolysis to obtain corresponding glycosyl-1-hydrogen phosphite monoester; 2, carrying out silylation on the glycosyl-1-hydrogen phosphite monoester by N,O-bi(trimethylsilyl)acetamide to obtain a trialkylphosphite intermediate, carrying out oxidation on an organic alkali/iodine simple substance system and carrying out in-situ hydrolysis to obtain glycosyl-1-monophosphate protected by acetyl; 3, removing an acetyl protecting group through sodium methylate and obtaining corresponding the high-purity glycosyl-1-monophosphate through sephadex chromatographic purification and ion exchange. According to the method disclosed by the invention, the glycosyl-1-monophosphate is obtained through the three steps and the total yield can reach 75 percent to 85 percent. Loss caused by benzyl removing by hydrogenation in a conventional method is avoided. The method disclosed by the invention is particularly suitable for preparing a great amount of glycosyl-1-monophosphate.

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Tetrahydropyran – Wikipedia,
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9/27/21 News A new application about 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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The total synthesis of D-erythro-sphingosine (9) was performed by a chirospecific method starting from D-galactose via an azidosphingosine intermediate to give highly homogeneous ( > 99.9% C18:1) sphingosine base (9) which contained no observable olefin isomerization by product and was demonstrated to be optically pure by a novel method utilizing Mosher’s acid. Ceramide (10) was prepared from this sphingosine (9) with highly homogeneous (99.8% C16:0) palmitic acid by two methods. The cerebroside glucosylceramide (23) was the next sphingolipid in this series to be synthesized in a highly homogeneous form. These three sphingolipids are currently being used for biophysical studies of the structures of their hydrated bio-molecular assemblies.

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9/27 News What Kind of Chemistry Facts Are We Going to Learn About 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

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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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(Chemical Equation Presented) The first O-glycosylation of hydroxamic acids is reported. This process involves the use of glycosyl N-phenyl trifluoroacetimidates as glycosyl donors in the presence TMSOTf and 4 A molecular sieves in dichloromethane. Under such conditions, a wide range of new glycosyl donors including glucosyl, galactosyl, mannosyl, glucuronyl, and ribosyl hydroxamates were prepared in good to high yields. This procedure appears to be an advantageous alternative for the synthesis of glycosyl hydroxamates of biological interest.

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An efficient method was reported for preparation of N-arylglycosyl-amines in aqueous THF under reflux in good yields. The factors affecting the configuration of C1-substituents of N-aryglycosylamines was investigated, that is, the influence of solvents, substituents of aromatic amines, and protecting groups of monosaccharides on the ratio of alpha- and beta-N-arylglycosylamines.

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A convenient methodology has been developed for the selective removal of the anomeric acyl group of carbohydrate derivatives using HClO4-SiO2 under acidic reaction conditions. Anomeric benzoyl groups can also be removed selectively following similar reaction conditions. The yields were excellent in all cases.

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