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.

NOVEL BENZIMIDAZOLE DERIVATIVES, PREPARATION METHOD THEREOF AND USE THEREOF AS ANTI-CANCER AGENT COMPRISING THE SAME

According to the present invention, there are provided a benzimidazole carbamate-sugar compound conjugate compound represented by the following Chemical Formula 1, a preparation method thereof, and a use thereof as an anti-cancer agent: Wherein, R1, R2, R3 and X are as defined in the specification and claims.

Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan

Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.