79580-70-4

Usage

Uses

Used in Enzyme Inhibition:
METHYL 2,3,6-TRI-O-BENZOYL-4-O-TRIFLUOROMETHANESULFONONYL-A-D-GALACTOPYRANOSIDE is used as an inhibitor of cellulases, which are enzymes that break down cellulose, a major component of plant cell walls. By inhibiting the activity of cellulases, METHYL 2,3,6-TRI-O-BENZOYL-4-O-TRIFLUOROMETHANESULFONONYL-A-D-GALACTOPYRANOSIDE can be employed in various applications where the degradation of cellulose needs to be controlled or prevented.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 2,3,6-TRI-O-BENZOYL-4-O-TRIFLUOROMETHANESULFONONYL-A-D-GALACTOPYRANOSIDE can be used as a starting material or intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique structure and chemical properties make it a valuable component in the development of new medications.
Used in Chemical Research:
METHYL 2,3,6-TRI-O-BENZOYL-4-O-TRIFLUOROMETHANESULFONONYL-A-D-GALACTOPYRANOSIDE can also be used in chemical research as a model compound to study the interactions between enzymes and their substrates. Its ability to inhibit cellulases can provide valuable insights into the mechanisms of enzymatic reactions and help in the design of more effective enzyme inhibitors.
Used in Agriculture:
In agriculture, METHYL 2,3,6-TRI-O-BENZOYL-4-O-TRIFLUOROMETHANESULFONONYL-A-D-GALACTOPYRANOSIDE can be employed as a tool to control the degradation of cellulose in crops, which can help in preserving the structural integrity of plants and improving crop yield. By inhibiting cellulases, METHYL 2,3,6-TRI-O-BENZOYL-4-O-TRIFLUOROMETHANESULFONONYL-A-D-GALACTOPYRANOSIDE can also be used to protect crops from pests and diseases that rely on cellulase activity for their survival.

Upstream product

• 98-88-4 benzoyl chloride 
• 3396-99-4 methyl α-D-galactopyranoside 
• 3601-36-3 methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 81905-39-7 methyl 2,3,6-tri-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-α-D-glycopyranosyl)-4-thio-α-D-glucopyranoside 
• 74593-34-3 methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranoside 
• 13264-02-3 methyl 2,3,6-tri-O-benzoyl-4-S-cyano-4-thio-α-D-glucopyranoside 
• 575457-75-9 (2S,3S,4S,5R,6R)-3-Azido-4,5-bis-benzoyloxy-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-pyran-2-carboxylic acid 
• 575457-73-7 C₂₄H₂₁N₅O₈ 
• 575457-72-6 C₂₆H₂₃N₅O₉ 
• 57784-06-2 methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 
• 1315206-06-4 methyl α-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl-(1->4)-β-(2,3,6-tri-O-acetyl-D-glucopyranosyl)-(1->4)-β-2,3,6-tri-O-benzoyl)-4-thio-D-glucoside 
• 118868-80-7 methyl 2,3,6-tri-O-benzoyl-4-thio-α-D-glucopyranoside 
• 79580-77-1 1,3-di-O-acetyl-2,6-di-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-thio-D-glucopyranoside 
• 79580-74-8 methyl 2,6-di-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-thio-α-D-glucopyranoside 
• 79580-84-0 C₂₉H₂₈O₈S 
• 41897-46-5 methyl 2,3,6-tri-O-benzoyl-4-S-benzoyl-4-thio-α-D-glucopyranoside 
• 92051-21-3 1-O-acetyl-2,3,6-tri-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-thio-α,β-D-glucopyranose 

Relevant academic research and scientific papers

Total synthesis method for xinaomycin

The invention belongs to the technical field of pharmaceutical chemistry and organic synthesis, and aims to provide a chemical total synthesis method for xinaomycin. The method comprises the steps of:using D-galactose and the like as raw materials, firstly carrying out 8 steps of reactions to obtain a compound 14, then performing condensation on the compound 14 and uracil to obtain a compound 15,performing 4 steps of reactions to obtain a compound 19, performing condensation on the compound 19 and a compound 6 to obtain a compound 20, and finally removing an ester protecting group and a Cbzprotecting group in turn, so as to obtain the natural product xinaomycin. The total synthesis method of the present invention is a method for synthesizing the natural product xinaomycin for the firsttime. The total synthesis method has the advantages of high product purity, low cost, simple operation and the like.

The α-Thioglycoligase Derived from a GH89 α-N-Acetylglucosaminidase Synthesises α-N-Acetylglucosamine-Based Glycosides of Biomedical Interest

We report here on the preparation of a novel α-thioglycoligase that can be used for the fast and efficient synthesis of α-N-acetylglucosamine-based glycosides. Using the α-N-acetyl-glucosaminidase from Clostridium perfringens of family GH89 (according to the Carbohydrate Active Enzymes classification) as starting point, we prepared mutants in the acid/base residue glutamic acid 483 that were found to have different synthetic efficiencies (maximal yields >80% after 24 h) in the presence of an activated donor and suitable acceptors. The synthetic potential of the Glu483 alanine mutant as an α-thioglycoligase – only the third biocatalyst with this stereospecificity reported to date, and the first selective for the N-acetylglucosamine moiety – was demonstrated by producing for the first time N-acetyl-α-d-glucosaminyl azide and N-acetylglucosamine α-thioglycosides in high yields. To showcase the application of such compounds, we show that they offer the wild-type CpGH89 protection from thermal unfolding, demonstrating their potential as pharmacological chaperones for the treatment of mucopolysaccharidosis IIIB (Sanfilippo syndrome). (Figure presented.).

Stereoinversion of Stereocongested Carbocyclic Alcohols via Triflylation and Subsequent Treatment with Aqueous N,N-Dimethylformamide

A convenient method for the stereoinversion of secondary alcohols, applicable to stereocongested carbocyclic substrates, is reported. A simple three-step procedure, including triflylation of the hydroxy group, nucleophilic oxygenative displacement by the treatment with aqueous N,N-dimethylformamide (DMF), and methanolysis, allowed for efficient stereoinversion of various substrates, including sugar derivatives, in one pot.

Glucose positions affect the phloem mobility of glucose-fipronil conjugates

In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.

Glucose positions affect the phloem mobility of glucose-fipronil conjugates

In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.

Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models

Methyl amino-deoxy-glycosides with α- and β-gluco, α-galacto, or α-manno stereochemistry with the amino functionality in each of the four possible non-anomeric positions have been synthesized and their pKa values determined by titration. These

Syntheses of cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases

Cellotriose and cellotetraose analogues carrying cyclohexene rings were developed as molecular probes which are expected to mimic the transition state conformation of hydrolysis by cellulases. The cyclohexene ring was placed at the pyranose ring being expected to locate the -1 subsite of the enzyme. In order to evaluate these probes, sulfur derivatives of cellotriose and cellotetraose were also synthesized as the enzyme tolerant analogues which mimic the stable conformations of the natural cellulose. The binding assays using differential scanning calorimetry revealed that introduction of the cyclohexene ring is effective to the complexation with an endoglucanase, NCE5 from Humicola insolens.

INTERMEDIATES AND PROCESSES FOR THE PREPARATION OF FLUOROGLYCOSIDE DERIVATIVES

The present invention provides processes for producing (2S,3R,4R,5S,6R)-5-fluoro-6- hydroxymethyl-2-[4-(4-methoxy-benzyl)-5-trifluoromethyl-1H-pyrazol-3-yloxy]- tetrahydro-pyran-3,4-diol or a tautomer or hydrate thereof, of high purity and in a relatively

SN2 displacement of carbohydrate triflates by 9-oximes of erythromycin a and of a tylosin derivative

The preparation of 9-O-glycosyloxime derivatives of erythromycin A (1) and tylosin (2) is reported. Access to this new class of macrolides was achieved from (E)-9-oxime of erythromycin A (3) and 9-oxime of tylosin 20-(1,3-dithiane) (4), by successful disp

Synthesis and Enzyme Inhibitory Activity of Novel Glycosidase Inhibitors Containing Sulfur and Selenium

The syntheses of novel methyl maltoside analogues containing sulfur in the nonreducing ring and either oxygen, sulfur, or selenium atoms in the interglycosidic linkage are described.The compounds are substrate analogues for glucosidases and are of interes