605-81-2

Basic information

• Product Name: methyl 2,3,4,6-tetra-O-methyl-alpha-D-glucopyranoside
• Synonyms: methyl 2,3,4,6-tetra-O-methyl-alpha-D-glucopyranoside
• CAS NO: 605-81-2
• Molecular Formula: C₁₁H₂₂O₆
• Molecular Weight: 250.28878
• EINECS: 210-096-8
• Mol File: 605-81-2.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 313.42°C (rough estimate)
• Flash Point: 117.5°C
• Appearance: /
• Density: 1.1082
• Vapor Pressure: 0.00151mmHg at 25°C
• Refractive Index: 1.4466 (estimate)
• CAS DataBase Reference: methyl 2,3,4,6-tetra-O-methyl-alpha-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4,6-tetra-O-methyl-alpha-D-glucopyranoside(605-81-2)
• EPA Substance Registry System: methyl 2,3,4,6-tetra-O-methyl-alpha-D-glucopyranoside(605-81-2)

Safety Data

• Hazardous Substances Data: 605-81-2(Hazardous Substances Data)

Usage

General Description

Methyl 2,3,4,6-tetra-O-methyl-alpha-D-glucopyranoside is a chemical compound derived from glucose. It is a methylated form of alpha-D-glucopyranoside, with methyl groups attached to the 2, 3, 4, and 6 carbon atoms of the glucose molecule. methyl 2,3,4,6-tetra-O-methyl-alpha-D-glucopyranoside is often used as a protecting group in organic synthesis to prevent unwanted reactions at the hydroxyl groups of glucose. It is also utilized in the production of various pharmaceuticals and as a research tool in carbohydrate chemistry. Additionally, it has potential applications in the food and cosmetics industries due to its stability and ability to improve the properties of certain products.

InChI:InChI=1/C11H22O6/c1-12-6-7-8(13-2)9(14-3)10(15-4)11(16-5)17-7/h7-11H,6H2,1-5H3

Upstream product

• 186581-53-3 diazomethane 
• 108-24-7 acetic anhydride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 74-83-9 methyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 1825-62-3 ethyl trimethylsilyl ether 
• 3149-65-3 methyl 2,3,4,6-tetra-O-methyl-β-D-glucopyranoside 
• 67-56-1 methanol 
• 62327-60-0 phenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 64656-69-5 benzyl O-α-D-glucopyranosyl-(1->4)-β-D-glucopyranoside 
• 57631-96-6 C₂₆H₄₂O₁₁ 
• 19146-24-8 methyl 2,3,6-tri-O-methyl-4-O-(2,3,4,6-tetra-O-methyl-α-D-glucopyranosyl)-β-D-glucopyranoside 

Downstream Products

• 62327-60-0 phenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-glucopyranoside 
• 76707-53-4 phenyl 2,3,4,6-tetra-O-methyl-1-thio-α-D-glucopyranoside 
• 753490-95-8 2,4-dinitrophenyl 2,3,4,6-tetra-O-methyl-β-D-glucopyranoside 
• 154-58-5 1,5-anhydro-D-glucitol 

Relevant articles and documents

Mechanism of the reductive cleavage reaction of permethylated methyl D-glycopyranosides

The mechanism of the reductive cleavage reaction of permethylated methyl D-glycopyranosides was investigated by measuring the rate of reaction. Glycosides employed were of α-Glc, β-Glc, α-Man, α-Gal, and β-Gal. Seven silanes were used to explore the reactivities of the reducing agents as well as to examine the stereoelectronic effects of the agents. Trimethylsilyl trifluoromethanesulfonate was employed as catalyst. In general, the rates of β anomers were about twice as fast as those of the α anomers. The rates of anomerization were about five to ten times lower than those of reduction. A cyclic oxonium ion has been proposed as a sole intermediate for the reductive cleavage of the α-glycoside linkage, but the attack of the reducing agent on both cyclic and acyclic forms as well as on the substrate-Lewis acid complex seems to be involved for the β anomer. Copyright (C) 1999 Elsevier Science Ltd.

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Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease

Despite the rapidly increasing number of patients suffering from type 2 diabetes, Alzheimer's disease, and diabetes-induced dementia, there are no disease-modifying therapies that are able to prevent or block disease progress. In this work, we investigate the potential of nature-inspired glucosylpolyphenols against relevant targets, including islet amyloid polypeptide, glucosidases, and cholinesterases. Moreover, with the premise of Fyn kinase as a paradigm-shifting target in Alzheimer's drug discovery, we explore glucosylpolyphenols as blockers of Aβ-induced Fyn kinase activation while looking into downstream effects leading to Tau hyperphosphorylation. Several compounds inhibit Aβ-induced Fyn kinase activation and decrease pTau levels at 10 μM concentration, particularly the per-O-methylated glucosylacetophloroglucinol and the 4-glucosylcatechol dibenzoate, the latter inhibiting also butyrylcholinesterase and β-glucosidase. Both compounds are nontoxic with ideal pharmacokinetic properties for further development. This work ultimately highlights the multitarget nature, fine structural tuning capacity, and valuable therapeutic significance of glucosylpolyphenols in the context of these metabolic and neurodegenerative disorders.

Structural analysis of novel kestose isomers isolated from sugar beet molasses

Eight kestose isomers were isolated from sugar beet molasses by carbon-Celite column chromatography and HPLC. GC-FID and GC-MS analyses of methyl derivatives, MALD-TOF-MS measurements and NMR spectra were used to confirm the structural characteristics of the isomers. The 1H and 13C NMR signals of each isomer saccharide were assigned using COSY, E-HSQC, HSQC-TOCSY, HMBC and H2BC techniques. These kestose isomers were identified as α-D-fructofuranosyl-(2-> 2)-α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside, α-D-fructofuranosyl-(2-> 3)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside, α-D-fructofuranosyl-(2-> 4)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside, β-D-fructofuranosyl-(2- > 4)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside, β-D-fructofuranosyl-(2- > 3)-α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside, α-D-fructofuranosyl-(2- > 1)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside, α-D-fructofuranosyl-(2- > 6)-α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside, and α-D-fructofuranosyl-(2- > 6)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside. The former five compounds are novel saccharides.