13100-46-4

Basic information

• Product Name: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE
• Synonyms: TETRA-O-ACETYL-B-D-GLUCOPYRANOSE, 1,2,3,4-;BETA-D-GLUCOSE-2,3,4,5-TETRAACETATE;1,2,3,4-TETRAACETYL-BETA-D-GLUCOPYRANOSE;1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE;2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE;1,2,3,4-tetra-O-acetyl-B-D-*glucopyranose;beta-D-glucose 1,2,3,4-tetraacetate;1,2,3,4-Tetra-O-acetyl-beta-D-
• CAS NO: 13100-46-4
• Molecular Formula: C₁₄H₂₀O₁₀
• Molecular Weight: 348.3
• EINECS: 236-018-2
• Product Categories: Sugars, Carbohydrates & Glucosides;Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis;Carbohydrates
• Mol File: 13100-46-4.mol
• Article Data: 34

Chemical Properties

• Melting Point: 126-128 °C(lit.)
• Boiling Point: 418.4 °C at 760 mmHg
• Flash Point: 145.6 °C
• Appearance: White to Off-white/Powder
• Density: 1.33 g/cm³
• Vapor Pressure: 9.44E-09mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in chloroform
• PKA: 14.48±0.10(Predicted)
• CAS DataBase Reference: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE(13100-46-4)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE(13100-46-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13100-46-4(Hazardous Substances Data)

Usage

Description

2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE is a white to off-white powder that is a derivative of beta-D-glucopyranose, a monosaccharide. It is characterized by the presence of four acetyl groups attached to the hydroxyl groups at the 2, 3, 4, and 6 positions, which significantly alter its chemical properties compared to the parent compound.

Uses

Used in Research Applications:
2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE is used as a substrate in the study of inositol synthase, an enzyme involved in the biosynthesis of inositol. This application is crucial for understanding the enzyme's function and its role in various biological processes.
Used in Chemical Synthesis:
In the chemical industry, 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE is used for the preparation of anionic surfactants. These surfactants are important in the formulation of detergents, cleaners, and other products that require emulsifying, dispersing, or wetting properties. The acetylated glucose derivative serves as a key intermediate in the synthesis of these surfactants, contributing to their stability and effectiveness.

InChI:InChI=1/C14H20O10/c1-6(16)20-11-10(5-15)24-14(23-9(4)19)13(22-8(3)18)12(11)21-7(2)17/h10-15H,5H2,1-4H3

Upstream product

• 37074-90-1 1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose 
• 1600-27-7 mercury(II) diacetate 
• 56767-75-0 2,3,4-tri-O-acetyl-α-D-glucopyranosyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 108-98-5 thiophenol 
• 2280-44-6 D-Glucose 
• 492-62-6 alpha-D-glucopyranose 
• 54325-28-9 6-O-trityl-α-D-glucose 
• 54325-28-9 (2R,3R,4S,5S,6R)-6-Trityloxymethyl-tetrahydro-pyran-2,3,4,5-tetraol 
• 604-69-3 β-D-glucose pentaacetate 
• 54325-28-9 6-O-trityl-D-glucopyranose 
• 67919-36-2 1,2,3,4-tetra-O-acetyl-6-O-trityl-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 492-61-5 β-D-glucose 

Downstream Products

• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 123814-34-6 O¹,O²,O³,O⁴-Tetraacetyl-O⁶-(bis-benzyloxy-phosphoryl)-β-D-glucopyranose 
• 4752-94-7 O¹,O²,O³,O⁴-tetraacetyl-O⁶-(tri-O-acetyl-2-benzoylamino-2-deoxy-β-D-glucopyranosyl)-β-D-glucopyranose 
• 71208-20-3 1,2,3,4-tetra-O-acetyl-6-O-benzoyl-β-D-glucopyranose 
• 114510-26-8 O¹,O²,O³,O⁴-Tetraacetyl-O⁶-phenylcarbamoyl-β-D-glucopyranose 
• 28154-38-3 O¹,O²,O³,O⁴-tetraacetyl-O⁶-methanesulfonyl-β-D-glucopyranose 
• 6619-10-9 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-β-D-glucopyranose 
• 108321-48-8 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 6-diphenylphosphate 
• 56-73-5 D-glucose 6-phosphate 
• 4613-78-9 β-D-gentiobiose octaacetate 
• 32449-92-6 D-glucurono-6,3-lactone 
• 13242-55-2 2,3,4-tri-O-acetyllevoglucosan 
• 39706-70-2 O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-O-1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 
• 10225-48-6 1,2,3,4-tetra-O-acetyl-6-bromo-6-deoxy-β-D-glucopyranose 

Relevant articles and documents

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Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

Synthetic method of gentiobiose

The invention provides a synthetic method of gentiobiose. The synthetic method of the gentiobiose comprises the following steps: taking D-glucose as a starting material; respectively synthesizing into beta-1,2,3,4-tetra-acetylated glucose and glucose-B-glucosinolate; and carrying out coupled reaction and then carrying out deprotection to generate the gentiobiose. The controllability of the technological process is high, isomerization of the product is avoided, the yield of single-step reaction is high, and the gentiobiose is suitable for being produced on a large scale. The separating efficiency of a final product is improved. By the chemical method, large-scale production of the gentiobiose is implemented, a biological-method complicated purification process is overcome, the production period is shortened, the cost is reduced, and the purity of the product is improved.