6748-91-0

Basic information

• Product Name: METHYL-2,3-DI-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: METHYL-2,3-DI-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE;Methyl-2,3-di-o-benzylidene-alpha-D-glucopyranoside;Methyl-4,6-di-O-benzylidene-2,3-di-O-benzoyl-α-D-glucopyranoside;Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside ,98%;Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-a-D-glucopyranoside;Methyl 2,3-Di-O-benzoyl-4,6-O-benzylidene-α[(4aS,6S,7S,8S,8aR)-7-benzoyloxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS NO: 6748-91-0
• Molecular Formula: C₂₈H₂₆O₈
• Molecular Weight: 490.5
• Product Categories: Carbohydrates
• Mol File: 6748-91-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 152.0 to 157.0 °C
• Boiling Point: 619.819 °C at 760 mmHg
• Flash Point: 264.493 °C
• Appearance: /
• Density: 1.332 g/cm³
• Refractive Index: 1.618
• CAS DataBase Reference: METHYL-2,3-DI-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-2,3-DI-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE(6748-91-0)
• EPA Substance Registry System: METHYL-2,3-DI-O-BENZOYL-4,6-O-BENZYLIDENE-ALPHA-D-GLUCOPYRANOSIDE(6748-91-0)

Safety Data

• Hazardous Substances Data: 6748-91-0(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

InChI:InChI=1/C28H26O8/c1-31-28-24(35-26(30)19-13-7-3-8-14-19)23(34-25(29)18-11-5-2-6-12-18)22-21(33-28)17-32-27(36-22)20-15-9-4-10-16-20/h2-16,21-24,27-28H,17H2,1H3/t21-,22+,23-,24-,27?,28-/m0/s1

Upstream product

• 98-88-4 benzoyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 1185860-21-2 methyl-[O⁴,O⁶-((S)-benzylidene)-β-D-gulopyranoside] 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 93-58-3 benzoic acid methyl ester 
• 4463-33-6 1,2-dimethoxy-3-methylbenzene 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 93-97-0 benzoic acid anhydride 
• 100-52-7 benzaldehyde 
• 4137-35-3 methyl 2,3-di-O-benzoyl-α-D-glucopyranoside 
• 611-74-5 N,N-dimethylbenzamide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 2397-26-4 N,N-dimethyl(chlorophenylmethylene)ammonium chloride 

Downstream Products

• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 33535-04-5 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 28642-64-0 methyl 4,6-O-benzylidene-2-O-benzoyl-α-D-glucopyranoside 
• 23477-56-7 methyl 4-O-benzyl-α-D-glucopyranoside 
• 20839-38-7 methyl 6-O-benzyl-α-D-glucopyranoside 
• 79330-96-4 phenyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-1-thio-β-D-glucopyranoside 
• 4137-35-3 methyl 2,3-di-O-benzoyl-α-D-glucopyranoside 
• 1174889-94-1 (2S,3S,4S,5R,6S)-3,4,5-tris(benzoyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid 
• 51236-52-3 methyl 2,3-di-O-benzoyl-6-deoxy-α-D-glucopyranoside 
• 1415663-31-8 5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A?11,12-cyclic carbonate 
• 1415663-30-7 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate 

Relevant articles and documents

SnCl2-Catalyzed Acetalation/Selective Benzoylation Sequence for the Synthesis of Orthogonally Protected Glycosyl Acceptors

Based on SnCl2-catalyzed acetalation and selective benzoylation, a one-pot strategy to efficiently synthesize orthogonally protected glycosyl acceptors with 2-OH/3-OH was developed. Consequently, 2-OBz or 3-OBz 4,6-O-benzylidene galactosides and glucosides were efficiently prepared in moderate to high yields starting from free galactosides and glucosides, and were used as valuable glycosyl acceptors for the synthesis of blood group antigens O and B analogues in this study.

Highly Regioselective Monoacylation of Unprotected Glucopyranoside Using Transient Directing-Protecting Groups

The regioselective functionalization of monosaccharides is notoriously achieved using metal catalysis, lengthy synthetic strategies requiring protection/deprotection, various enzymes, or other methods that target cis-diols (and thus cannot be used with glucopyranose derivatives), In this paper, we report a new method using selected boronic acids as temporary protecting groups, and describe its application to the regioselective functionalization of methyl α-d-glucopyranoside, the most difficult monosaccharide to functionalize regioselectively. Generally, reactions of glucopyranosides may lead to a plethora of mono- and polyfunctionalized derivatives, yet our method gave the 3-O-acetylated, 2-O-benzoylated, and 2-O-pivaloylated derivatives of methyl α-d-glucopyranoside as major products. We focused on the use of recyclable and green temporary protecting groups (in a one-pot reaction) and on the modulation of the intramolecular hydrogen-bonding network using selected arylboronic acids. A complete scalable procedure leading to a single regioisomer from unprotected methyl α-d-glucopyranoside is presented.

Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids

Direct oxidation of the 4,6-O-benzylidene acetal protecting group to C-6 carboxylic acid has been developed that provides an easy access to a wide range of biologically important and synthetically challenging uronic acid and sugar amino acid derivatives in good yields. The RuCl3-NaIO4-mediated oxidative cleavage method eliminates protection and deprotection steps and the reaction takes place under mild conditions. The dual role of the benzylidene acetal, as a protecting group and source of carboxylic acid, was exploited in the efficient synthesis of six-carbon sialic acid analogues and disaccharides bearing uronic acids, including glycosaminoglycan analogues.