19488-48-3

Basic information

• Product Name: methyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside
• Synonyms: a-D-Glucopyranoside, methyl 2,3,6-tri-O-(phenylmethyl)-
• CAS NO: 19488-48-3
• Molecular Formula: C₂₈H₃₂O₆
• Molecular Weight: 464.5501
• Mol File: 19488-48-3.mol
• Article Data: 78

Chemical Properties

• Boiling Point: 603.265°C at 760 mmHg
• Flash Point: 318.644°C
• Density: 1.209g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: ?20°C
• BRN: 1442492
• CAS DataBase Reference: methyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside(19488-48-3)
• EPA Substance Registry System: methyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside(19488-48-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19488-48-3(Hazardous Substances Data)

Upstream product

• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 620-05-3 iodomethylbenzene 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 29600-81-5 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 53685-11-3 (2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol 
• 100-44-7 benzyl chloride 
• 88819-23-2 Methyl 3,6-di-O-benzyl-α-D-galactopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 145933-55-7 methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-α-D-lyxo-hexopyranosyl-2-ulose 
• 51842-18-3 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 125084-93-7 methyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-formamido-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 86883-50-3 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-α-D-glucopyranoside 
• 86883-49-0 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-α-D-glucopyranoside 
• 77117-44-3 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 64694-18-4 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 84799-76-8 methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 744-05-8 methyl α-D-glucopyranosyl-(1->4)-α-D-glucopyranoside 
• 118579-76-3 methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 98906-48-0 methyl 2-O-acetyl-3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-1→4-(2,3,6-tri-O-benzyl)-β-D-glucopyranoside 
• 87871-03-2 methyl 2,3,6-tri-O-benzyl-4-deoxy-4-trifluoromethanesulfonyl-α-D-glucopyranoside 
• 74808-17-6 methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 71692-91-6 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 128503-40-2 methyl-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 154703-95-4 methyl 4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

Cleavage pattern of alkoxy- or aryloxymethyl ethers induced by mixed hydrides

-

A novel, reductive ring-opening of carbohydrate benzylidene acetals, with unusual regioselectivity

-

Methyl 4-O-β-D-galactopyranosyl α-D-glucopyranoside (methyl α-lactoside)

Methyl α-lactoside, C13H24O11, (I), is described by glycosidic torsion angles φ (O5gal-C1 gal-O1gal-C4glc) and Ψ (C1 gal-O1gal-C4glc-C5glc/

Streamlined access to carbohydrate building blocks: Methyl 2,4,6-tri-O-benzyl-α-D-glucopyranoside

Presented herein is an improved synthesis of a common 3-OH glycosyl acceptor. This compound is a building block that is routinely synthesized by many research groups to be used in glycosylation refinement studies. The only known direct synthesis by Koto lacks regioselectivity and relies on chromatography separation using hazardous solvents. Our improved synthetic approach relies on Koto's selective benzylation protocol, but it is followed by acylation-purification-deacylation sequence. Although this approach involves additional manipulations, it provides consistent results and is superior to other indirect strategies. Also obtained, albeit in minor quantities, is 4-OH acceptor, another common building block.

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.