53008-63-2

Basic information

• Product Name: Methyl 2,3,4,6-Tetra-O-benzyl-a-D-galactopyranoside
• Synonyms: Methly-2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside;Methyl 2,3,4,6-Tetrakis-O-(phenylMethyl)-α-D-galactopyranoside;(2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)Methyl)-6-Methoxytetrahydro-2H-pyran;Methyl 2,3,4,6-tetrakis-O-(phenylmethyl)-alpha-D-galactopyranoside
• CAS NO: 53008-63-2
• Molecular Formula: C₃₅H₃₈O₆
• Molecular Weight: 554.67
• EINECS: 1533716-785-6
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 53008-63-2.mol
• Article Data: 151

Chemical Properties

• Boiling Point: 656.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate, Methanol
• CAS DataBase Reference: Methyl 2,3,4,6-Tetra-O-benzyl-a-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3,4,6-Tetra-O-benzyl-a-D-galactopyranoside(53008-63-2)
• EPA Substance Registry System: Methyl 2,3,4,6-Tetra-O-benzyl-a-D-galactopyranoside(53008-63-2)

Safety Data

• Hazardous Substances Data: 53008-63-2(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Oil

Uses

Methyl 2,3,4,6-Tetra-O-benzyl-α-D-galactopyranoside (cas# 53008-63-2) is a compound useful in organic synthesis.

Upstream product

• 67-56-1 methanol 
• 96863-21-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate 
• 371766-59-5 2,3,4,6-tetra-O-benzyl-1-O-[N-allyl-thiocarbamoyl]-D-glucopyranose 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 126786-18-3 1-azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-mannopyranose 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 
• 100-44-7 benzyl chloride 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 3458-28-4 D-Mannose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 

Downstream Products

• 91510-87-1 2-methyl-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propene 
• 91510-87-1 2-methyl-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propene 
• 92413-81-5 3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)butene 
• 92413-82-6 2-bromo-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propene 
• 91602-61-8 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 78890-68-3 1-deoxy-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 35303-86-7 (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 61277-56-3 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranose 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 

Relevant articles and documents

Synthesis of C6′′-modified α-C-GalCer analogues as mouse and human iNKT cell agonists

α-GalCer analogues that combine known Th1 polarizing C6′′-modifications with a C-glycosidic linkage were synthesized. We employed a protecting group strategy that allowed the preparation of both saturated and unsaturated derivatives with variable C6′′-substituents. Selected analogues demonstrate promising activity in mice. Interestingly, the introduction of a 6′′-O-pyridinylcarbamoyl substituent to α-C-GalCer restores its antigenicity in human iNKT cells.

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.