120200-51-3

Basic information

• Product Name: methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside
• Synonyms: methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside
• CAS NO: 120200-51-3
• Molecular Weight: 490.51
• Mol File: 120200-51-3.mol

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside(120200-51-3)
• EPA Substance Registry System: methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside(120200-51-3)

Safety Data

• Hazardous Substances Data: 120200-51-3(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 93-97-0 benzoic acid anhydride 
• 1185860-21-2 methyl-[O⁴,O⁶-((S)-benzylidene)-β-D-gulopyranoside] 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 33535-04-5 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 4137-35-3 methyl 2,3-di-O-benzoyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 65-85-0 benzoic acid 
• 51224-39-6 methyl β-D-glucopyranoside 

Downstream Products

• 1174889-94-1 (2S,3S,4S,5R,6S)-3,4,5-tris(benzoyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid 
• 61553-58-0 methyl 4,6-di-O-acetyl-2,3,-di-O-benzoyl-α-D-glucopyranoside 
• 14169-22-3 methyl 2,3,4-tri-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside 
• 4137-35-3 methyl 2,3-di-O-benzoyl-α-D-glucopyranoside 
• 89539-31-1 methyl 2,3-di-O-benzoyl-4-O-benzyl-α-D-glucopyranoside 
• 57784-06-2 methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 
• 3396-68-7 methyl 2,3,6-tri-O-benzoyl-α-D-mannopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 51236-52-3 methyl 2,3-di-O-benzoyl-6-deoxy-α-D-glucopyranoside 

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.

Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope

This work reports stannous chloride (SnCl2)-catalyzed regio-/site-selective acylation with unusually broad substrate scope. In addition to 1,2- and 1,3-diols and glycosides containing cis-vicinal diol, the substrate scope also includes glycosides without cis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84-97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst for regio-/site-selective acylation compared with any previously reported reagents. This journal is

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.

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.

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.

Regioselective Benzoylation of 4,6-O-Benzylidene Acetals of Glycopyranosides in the Presence of Transition Metals

Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides by benzoic anhydride in acetonitrile in the presence of Cu(CF3COO)2 as a promoter gave 2-benzoates for α-D-glucopyranosides and α-D-mannopyranosides and 3-benzoates for β-D-galactopyranosides in good yields with high regioselectivity. Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides of D-galactose and D-mannose by benzoyl chloride in the presence of MoO2(acac)2 as a catalyst in all studied cases led to regioselective 3-substitution.

Synthesis and antibacterial activity of novel modified 5-O-desosamine ketolides

A series of novel modified 5-O-desosamine-ketolides were synthesized. The 5-O-desosamine fragment was removed from ketolide by an efficient and mild manipulation. 4-O-substituted desosamine was introduced into the ketolide aglycon and various coupling methods were essayed for the glycosylation. Three novel ketolides were tested for in vitro antibacterial activity against a panel of susceptible and resistant pathogens. Compound 26 showed potent activity against all the methicillin-sensitivity and resistant pathogens.

2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks

Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process and wide application range are a few advantages of the current process.

FeCl3 mediated arylidenation of carbohydrates

Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl3-catalyzed (20 mol %) regioselective 4,6-O-arylidenation producing the corresponding acetals in high yields. FeCl3 also mediates acetalation of glycosides and thioglycosides of cellobiose, maltose, and lactose affording the corresponding 4′,6′-O-benzylidene acetals, which were isolated after their acetylation in situ with acetic anhydride and pyridine. The combined yields (two steps) of these final products are also high (61-84%). The procedure is applicable to a wide variety of functional groups including -OBn.

Synthesis and structural analysis of a series of d-glucose derivatives as low molecular weight gelators

Low molecular weight gelators are an interesting new type of compounds that are important in supramolecular chemistry and advanced materials. Previously, we had synthesized several acyl derivatives of methyl 4,6-O-benzylidene-α-d-glucopyranoside and found