25577-40-6

Basic information

• Product Name: Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside
• Synonyms: Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside;Methyl 2-O-acetyl-4,6-O-benzylidene-alpha-D-glucopyranoside;Methyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS NO: 25577-40-6
• Molecular Formula: C₁₆H₂₀O₇
• Molecular Weight: 324.3258
• Mol File: 25577-40-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 133-134 °C(Solv: ethyl ether (60-29-7); pentane (109-66-0))
• Boiling Point: 471.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• PKA: 12.49±0.70(Predicted)
• CAS DataBase Reference: Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside(25577-40-6)
• EPA Substance Registry System: Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside(25577-40-6)

Safety Data

• Hazardous Substances Data: 25577-40-6(Hazardous Substances Data)

Usage

General Description

Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside is a synthetic compound with the chemical formula C20H22O7. It is a derivative of glucose and is commonly used in organic chemistry and pharmaceutical research. Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside is often used as a starting material for the synthesis of other organic compounds, and its structure makes it useful for studying the reactivity and behavior of glucose derivatives. Methyl 2-O-acetyl-4,6-O-benzylidene-a-D-glucopyranoside may also have potential applications in drug development and in the production of natural product derivatives.

Upstream product

• 2774-22-3 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 141-78-6 ethyl acetate 
• 108-24-7 acetic anhydride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 110-86-1 pyridine 
• 439-06-5 methyl-[O²-acetyl-O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside] 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 26295-65-8 (4aR,6S,7S,8S,8aR)-7,8-Bis-(1-ethoxy-ethoxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 4148-58-7 (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Downstream Products

• 87924-30-9 methyl 3-O-acetyl-4,6-O-benzylidene-α-D-allopyranoside 
• 116391-13-0 methyl 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside 
• 129165-16-8 Ammonium methyl 3-O-sulfo-α-D-glucopyranoside 
• 42400-52-2 methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate 
• 87924-27-4 methyl 2-O-acetyl-4,6-O-benzylidene-3-O-triflyl-α-D-glucopyranoside 
• 7115-19-7 methyl β-D-glucopyranosyl-<1->3>-α-D-glucopyranoside 
• 35311-35-4 methyl-[O²-acetyl-O⁴,O⁶-((R)-benzylidene)-O³-methyl-α-D-glucopyranoside] 
• 2872-57-3 methyl-[O²-acetyl-O⁴,O⁶-((R)-benzylidene)-O³-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 75996-21-3 methyl-[O²-acetyl-O³-benzoyl-O⁴,O⁶-((R)-benzylidene)-α-D-glucopyranoside] 

Relevant articles and documents

Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts

Herein, we report the oligopeptide-catalyzed site-selective acylation of partially protected monosaccharides. We identified catalysts that invert site-selectivity compared to N-methylimidazole, which was used to determine the intrinsic reactivity, for 4,6

DBN-Catalyzed Regioselective Acylation of Carbohydrates and Diols in Ethyl Acetate

The 1,5-diazabicyclo[4.3.0]non-5-ene (DBN)-catalyzed regioselective acylation of carbohydrates and diols in ethyl acetate has been developed. The hydroxyl groups can be selectively acylated by the corresponding anhydride in EtOAc in the presence of a catalytic amount (as low as 0.1 equiv.) of DBN at room temperature to 40 °C. This method avoids metal catalysts and toxic solvents, which makes it comparatively green and mild, and it uses less organic base compared with other selective acylation methods. Mechanism studies indicated that DBN could catalyze the selective acylation of hydroxyl moieties through a dual H-bonding interaction.

Enhanced site-selectivity in acylation reactions with substrate-optimized catalysts on solid supports

A concept for site selective acylation of poly-hydroxylated substrates is presented where polymer-supported catalysts are employed: catalytically active DMAP units were combined with a library of small molecule peptides attached to the solid phase with the goal to identify substrate-optimized catalysts through library screening. For selected examples, we demonstrate how the optimized catalysts can convert “their” substrate with a markedly enhanced site-selectivity, compared to only DMAP. Due to the solid support, product purification is significantly simplified, and the peptidic catalysts can be easily reused in multiple cycles while conserving its efficiency.