604-70-6

Usage

Uses

Used in Organic Synthesis:
METHYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is used as a key intermediate in the synthesis of complex organic compounds. Its versatile structure allows for the creation of a wide range of molecules, making it a valuable asset in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is used as a building block for the development of new drugs. Its unique structure can be modified to create molecules with specific biological activities, potentially leading to the discovery of novel therapeutic agents.
Used in Chemical Research:
METHYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is also used in chemical research to study the properties and reactions of complex organic molecules. Its unique structure provides researchers with valuable insights into the behavior of similar compounds, contributing to the advancement of chemical knowledge.
Used in Material Science:
In the field of material science, METHYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE can be used to develop new materials with specific properties. Its ability to form complex structures makes it a promising candidate for the creation of advanced materials with applications in various industries.
Overall, METHYL-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE is a versatile compound with a wide range of applications across different industries, including organic synthesis, pharmaceuticals, chemical research, and material science. Its unique structure and properties make it an invaluable asset in the development of new compounds and materials.

Upstream product

• 108-24-7 acetic anhydride 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 5019-25-0 methyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 20701-50-2 α,D-methyl-3,4,6-tri-O-acetyl-2-deoxy-2β-iodoglucopyranoside 
• 67-56-1 methanol 
• 83-87-4 D-Mannose pentaacetate 
• 67-66-3 chloroform 
• 7550-45-0 titanium tetrachloride 
• 13242-53-0 acetobromomannose 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 3458-28-4 D-Mannose 
• 50692-55-2 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-mannopyranoside 
• 141-78-6 ethyl acetate 

Downstream Products

• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 3427-45-0 phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 4201-66-5 methyl 6-O-acetyl-α-D-glucopyranoside 
• 50694-97-8 2,6-di-O-Ac-α-D-Glc 
• 51842-31-0 methyl 4,6-di-O-acetyl-α-D-glucopyranoside 
• 51295-60-4 methyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside 
• 50694-98-9 methyl 3,6-di-O-acetyl-α-D-glucopyranoside 
• 18031-51-1 methyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside 
• 79-20-9 acetic acid methyl ester 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 91602-61-8 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 

Relevant academic research and scientific papers

1,2-Acyloxyl Migration in Pyranosyl Radicals

Tetra-O-acetylgalactosyl radical (5) and tetra-O-acetylglucosyl radical (10) undergo a 1,2-migration of acetoxyl groups to the corresponding 2-deoxytetra-O-acetylpyranosan-2-yl radicals.The activation parameters for the rearrangement of tetra-O-acetylgalactosyl radical, as determined by ESR spectroscopy, are ΔH(excit.) = 12.2 +/- 0.3 kcal/mol and ΔS(excit.) = -6.7 +/- 1.0 eu.Labeling studies with 18 O support a five-membered cyclic transition state for the rearrangement with exchange of the oxygen atoms of the carboxy group.The driving force for the rearrangement, which is unfavorable in terms of the stability of the radical centers, derives from the gain in anomeric stabilization of the product radical.

Pachymoside A - A novel glycolipid isolated from the marine sponge Pachymatisma johnstonia

Crude extracts of the North Sea marine sponge Pachymatisma johnstonia showed promising activity in a new assay for inhibitors of bacterial type III secretion. Bioassay-guided fractionation resulted in the isolation of the pachymosides, a new family of sponge glycolipids. A major part of the structural diversity in this family of glycolipids involves increasing degrees of acetylation and differing positions of acetylation on a common pachymoside glycolipid template. All of the metabolites with these variations in acetylation pattern were converted into the same peracetylpachymoside methyl ester (2) for purification and spectroscopic analysis. Pachymoside A (1) is the component of the mixture that has natural acetylation at the eight galactose hydroxyls and at the C-6 hydroxyls of glucose-B and glucose-D. Chemical degradation and transformation in conjunction with extensive analysis of 800 MHz NMR data was used to elucidate the structure of pachymoside A (1).

Probing the Transition States of Four Glucoside Hydrolyses with 13C Kinetic Isotope Effects Measured at Natural Abundance by NMR Spectroscopy

Kinetic isotope effects (KIEs) were measured for methyl glucoside (4) hydrolysis on unlabeled material by NMR. Twenty-eight 13C KIEs were measured on the acid-catalyzed hydrolysis of α-4 and β-4, as well as enzymatic hydrolyses with yeast α-glucosidase and almond β-glucosidase. The 1-13C KIEs on the acid-catalyzed reactions of α-4 and β-4, 1.007(2) and 1.010(6), respectively, were in excellent agreement with the previously reported values (1.007(1), 1.011(2): Bennet and Sinnott, J. Am. Chem. Soc. 1986, 108, 7287). Transition state analysis of the acid-catalyzed reactions using the 13C KIEs, along with the previously reported 2H KIEs, confirmed that both reactions proceed with a stepwise DN*AN mechanism and showed that the glucosyl oxocarbenium ion intermediate exists in an E3 sofa or 4H3 half-chair conformation. 13C KIEs showed that the α-glucosidase reaction also proceeded through a D N*AN mechanism, with a 1-13C KIE of 1.010(4). The secondary 13C KIEs showed evidence of distortions in the glucosyl ring at the transition state. For the β-glucosidase-catalyzed reaction, the 1-13C KIE of 1.032(1) demonstrated a concerted A NDN mechanism. The pattern of secondary 13C KIEs was similar to the acid-catalyzed reaction, showing no signs of distortion. KIE measurement at natural abundance makes it possible to determine KIEs much more quickly than previously, both by increasing the speed of KIE measurement and by obviating the need for synthesis of isotopically labeled compounds.

General Strategy for the Synthesis of Rare Sugars via Ru(II)-Catalyzed and Boron-Mediated Selective Epimerization of 1,2- trans-Diols to 1,2- cis-Diols

Human glycans are primarily composed of nine common sugar building blocks. On the other hand, several hundred monosaccharides have been discovered in bacteria and most of them are not readily available. The ability to access these rare sugars and the corresponding glycoconjugates can facilitate the studies of various fundamentally important biological processes in bacteria, including interactions between microbiota and the human host. Many rare sugars also exist in a variety of natural products and pharmaceutical reagents with significant biological activities. Although several methods have been developed for the synthesis of rare monosaccharides, most of them involve lengthy steps. Herein, we report an efficient and general strategy that can provide access to rare sugars from commercially available common monosaccharides via a one-step Ru(II)-catalyzed and boron-mediated selective epimerization of 1,2-trans-diols to 1,2-cis-diols. The formation of boronate esters drives the equilibrium toward 1,2-cis-diol products, which can be immediately used for further selective functionalization and glycosylation. The utility of this strategy was demonstrated by the efficient construction of glycoside skeletons in natural products or bioactive compounds.

Structure of the unusual Sinorhizobium fredii HH103 lipopolysaccharide and its role in symbiosis

Rhizobia are soil bacteria that form important symbiotic associations with legumes, and rhizobial surface polysaccharides, such as K-antigen polysaccharide (KPS) and lipopolysaccharide (LPS), might be important for symbiosis. Previously, we obtained a mutant of Sinorhizobium fredii HH103, rkpA, that does not produce KPS, a homopolysaccharide of a pseudaminic acid derivative, but whose LPS electrophoretic profile was indistinguishable from that of the WT strain. We also previously demonstrated that the HH103 rkpLMNOPQ operon is responsible for 5-acetamido-3,5,7,9-tetradeoxy-7-(3-hydroxybutyramido)-L-glyc-ero-L-manno-nonulosonic acid [Pse5NAc7(3OHBu)] production and is involved in HH103 KPS and LPS biosynthesis and that an HH103 rkpM mutant cannot produce KPS and displays an altered LPS structure. Here, we analyzed the LPS structure of HH103 rkpA, focusing on the carbohydrate portion, and found that it contains a highly heterogeneous lipid A and a peculiar core oligosaccharide composed of an unusually high number of hexuronic acids containing b-configured Pse5NAc7(3OHBu). This pseudaminic acid derivative, in its a-configuration, was the only structural component of the S. fredii HH103 KPS and, to the best of our knowledge, has never been reported from any other rhizobial LPS. We also show that Pse5NAc7(3OHBu) is the complete or partial epitope for a mAb, NB6-228.22, that can recognize the HH103 LPS, but not those of most of the S. fredii strains tested here. We also show that the LPS from HH103 rkpM is identical to that of HH103 rkpA but devoid of any Pse5NAc7(3OHBu) residues. Notably, this rkpM mutant was severely impaired in symbiosis with its host, Macroptilium atropurpureum.

Direct dehydrative glycosylation catalyzed by diphenylammonium triflate

Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation

This work demonstrates the utilization of phosphotungstic acid (PTA) as a novel acidic catalyst for carbohydrate reactions, such as per-O-acetylation, regioselective O-4,6 benzylidene acetal formation, regioselective O-4 ring-opening, and glycosylation. These reactions are basic and salient during the synthesis of carbohydrate-based bioactive oligomers. Phosphotungstic acid's high acidity and eco-friendly character make it a tempting alternative to corrosive homogeneous acids. The various homogenous acid catalysts were replaced by the phosphotungstic acid solely for different carbohydrate reactions. It can be widely used as a catalyst for organic reactions as it is thermally stable and easy to handle. In our work, the reactions are operated smoothly under ambient conditions; the temperature varies from 0 °C to room temperature. Good to excellent yields were obtained in all four kinds of reactions.

ACYLATED ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF AUTOIMMUNE DISORDERS

Disclosed herein are acylated active agents (e.g., acylated catechin polyphenols, acylated carotenoids, acylated mesalamines, acylated sugars, acylated shikimic acids, acylated ellagic acid, acylated ellagic acid analogue, and acylated hydroxybenzoic acids), active agent combinations (e.g., with a second agent that is a fatty acid) and methods of their use, e.g., for modulating an autoimmunity marker or for treating an autoimmune disorder.

Structural properties of D-mannopyranosyl rings containing O-Acetyl side-chains

The crystal structures of 1,2,3,4,6-penta-O-Acetyl--d-mannopyranose, C16H22O11, and 2,3,4,6-Tetra-O-Acetyl--d-mannopyranosyl-(1.2)-3,4,6-Tri-O-Acetyl--d-mannopyranosyl-( 1.3)-1,2,4,6-Tetra-O-Acetyl--d-mannopyranose, C40H54O27, were determined and compared to those of methyl 2,3,4,6-Tetra-O-Acetyl--d-mannopyranoside, methyl -d-mannopyranoside andmethyl -d-mannopyranosyl-(1.2)--d-mannopyranoside to evaluate the effects of O-Acetylation on bond lengths, bond angles and torsion angles. In general, O-Acetylation exerts little effect on the exo-and endocyclic C-C and endocyclic C-O bond lengths, but the exocyclic C-O bonds involved in O-Acetylation are lengthened by -0.02 A ° . The conformation of the O-Acetyl side-chains is highly conserved, with the carbonyl O atom either eclipsing the H atom attached to a 2-Alcoholic C atom or bisecting the H-C-H bond angle of a 1-Alcoholic C atom. Of the two C-O bonds that determine O-Acetyl side-chain conformation, that involving the alcoholic C atom exhibits greater rotational variability than that involving the carbonyl C atom. These findings are in good agreement with recent solution NMR studies of O-Acetyl side-chain conformations in saccharides. Experimental evidence was also obtained to confirm density functional theory (DFT) predictions of C-O and O-H bond-length behavior in a C-O-H fragment involved in hydrogen bonding.

Calcium hypophosphite mediated deiodination in water: Mechanistic insights and applications in large scale syntheses of d-quinovose and d-rhamnose

The inorganic calcium hypophosphite was found to be a cheap, non-toxic, water-soluble and environmentally friendly reducing reagent for radical deiodination in water. Thorough mechanism studies revealed that calcium hypophosphite was oxidized to water insoluble calcium phosphite which was the major co-product of the deiodination reaction. Based on this observation, a practical synthesis of rare d-quinovose and d-rhamnose from cheap and commercially available materials on a hundred-mmol scale was reported.