51842-18-3

Basic information

• Product Name: Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-mannopyranoside
• Synonyms: Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-mannopyranoside;Methyl 2,3-di-O-benzyl-4,6-O-benzylidene-a-D-mannopyranoside;Methyl 2,3-bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)-alpha-D-mannopyranoside
• CAS NO: 51842-18-3
• Molecular Formula: C₂₈H₃₀O₆
• Molecular Weight: 462.539
• Product Categories: Carbohydrates
• Mol File: 51842-18-3.mol
• Article Data: 89

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-mannopyranoside(51842-18-3)
• EPA Substance Registry System: Methyl-4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-mannopyranoside(51842-18-3)

Safety Data

• Hazardous Substances Data: 51842-18-3(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 56-23-5 tetrachloromethane 
• 2774-22-3 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside 
• 100-39-0 benzyl bromide 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 67-56-1 methanol 
• 1000813-65-9 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 774-48-1 (diethoxymethyl)benzene 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 76375-66-1 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 93974-18-6 2-phenyl-1,3-dithiane-1-oxide 

Downstream Products

• 6988-40-5 methyl 2,3-di-O-benzyl-α-D-mannopyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 15038-71-8 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 2774-19-8 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 57784-06-2 methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides

A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is

Synthesis of methyl 4,6-di-o-ethyl-α-d-glucopyranoside-based azacrown ethers and their effects in asymmetric reactions

Carbohydrate-based crown ethers have been reported to be able to generate asymmetric induction in certain reactions. Previously, it was proved that the monosaccharide unit, the anomeric substituent, and the sidearm could influence the catalytic activity of the monoaza-15-crown-5 macrocycles derived from sugars. In order to gain information about the effect of the flexibility, 4,6-di-O-ethyl-glucoside-based crown compounds were synthesized, and their efficiency was compared to the 4,6-O-benzylidene analogues. It was found that the absence of the two-ring annulation has a negative effect on the enantioselectivity in liquid-liquid two-phase reactions: in the Darzens condensation of 2-chloroacetophenone and in the epoxidation of chalcone. The same trend was observed in the solid-liquid phase Michael addition of diethyl acetamidomalonate. Surprisingly, in the solid-liquid phase cyclopropanation of benzylidenemalononitrile, one of the new catalysts was highly enantioselective (99% ee).