4860-85-9

Basic information

• Product Name: METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE
• Synonyms: METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE;1-O-Methyl-β-D-glucopyranose 2,3,4,6-tetraacetate;Methyl β-D-glucopyranoside tetraacetate;[3,5-diacetyloxy-2-(acetyloxymethyl)-6-methoxyoxan-4-yl] acetate;[3,5-diacetyloxy-2-(acetyloxymethyl)-6-methoxy-oxan-4-yl] ethanoate;acetic acid [3,5-diacetoxy-2-(acetoxymethyl)-6-methoxy-tetrahydropyran-4-yl] ester;Methyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranose
• CAS NO: 4860-85-9
• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.33
• Mol File: 4860-85-9.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 407.3ºC at 760 mmHg
• Flash Point: 176.1ºC
• Appearance: /
• Density: 1.27 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE(4860-85-9)
• EPA Substance Registry System: METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE(4860-85-9)

Safety Data

• Hazardous Substances Data: 4860-85-9(Hazardous Substances Data)

Usage

General Description

Methyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside is a chemical compound that is commonly used as a building block in the synthesis of carbohydrates and glycosides. It is a derivative of glucose, a type of sugar, and is often employed as a protecting group in organic synthesis to selectively modify the reactivity of certain functional groups within a molecule. METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is also used in the preparation of pharmaceuticals and as a reagent in various biochemical and medicinal research applications. Its acetyl groups make it more stable and less reactive than glucose, allowing for greater control over chemical reactions and the selective modification of glucose-based molecules.

Upstream product

• 20701-50-2 α,D-methyl-3,4,6-tri-O-acetyl-2-deoxy-2β-iodoglucopyranoside 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 83-87-4 D-Mannose pentaacetate 
• 13242-53-0 acetobromomannose 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 3458-28-4 D-Mannose 
• 13265-84-4 D-glucal 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 172847-87-9 2',4',6'-Trimethoxyphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 604-69-3 β-D-glucose pentaacetate 
• 97-30-3 methyl D-glucopyranoside 

Downstream Products

• 2872-72-2 phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 20771-12-4 methyl 6-O-acetyl-β-D-glucopyranoside 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 30902-96-6 methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 1237738-01-0 isopropyl 3,4,6-tri-O-acetyl-α-D-glucopyranoside 
• 6586-70-5 α-isopropyl-2,3,4,6-tetra-O-acetyl-D-glucopyranoside 
• 15038-69-4 methyl β-D-glucopyranoside 2-benzyl ether 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 

Relevant articles and documents

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.

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.

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.