118711-43-6

Basic information

• Product Name: (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene
• Synonyms: (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene
• CAS NO: 118711-43-6
• Molecular Weight: 759.894
• Mol File: 118711-43-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene(118711-43-6)
• EPA Substance Registry System: (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene(118711-43-6)

Safety Data

• Hazardous Substances Data: 118711-43-6(Hazardous Substances Data)

Upstream product

• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 

Downstream Products

• 172340-50-0 (2S,3R,4E)-3-(benzoyloxy)-2-(hexadecanoylamino)-1-[(2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)oxy]-4-octadecene 
• 194299-30-4 (2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(2,3-di-O-benzoyl-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene 
• 1053254-44-6 (2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(2,6-di-O-benzoyl-4-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene 
• 172340-51-1 (2S,3R,4E)-3-(benzoyloxy)-2-(hexadecanoylamino)-1-[(2,3-di-O-benzoyl-β-D-galactopyranosyl)oxy]-4-octadecene 
• 194299-19-9 (2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-2,6-di-O-benzoyl-β-D-galactopyranosyl)oxy]-4-octadecene 
• 194299-29-1 (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3-di-O-benzoyl-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene 
• 172340-61-3 (2S,3R,4E)-3-Benzoyloxy-2-hexadecanoylamino-1-(2-O-benzoyl-3,4-O-isopropylidene-6-O-tertbutyldimethylsilyl-β-D-galactopyranosyloxy)-4-octadecene 
• 194299-20-2 (2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(2,6-di-O-benzoyl-β-D-galactopyranosyl)oxy]-4-octadecene 
• 172340-49-7 (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)oxy]-4-octadecene 
• 194299-18-8 (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-2,6-di-O-benzoyl-β-D-galactopyranosyl)oxy]-4-octadecene 
• 194299-28-0 (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3-di-O-benzoyl-β-D-galactopyranosyl)oxy]-4-octadecene 
• 172281-53-7 (2S,3R,4E)-3-(benzoyloxy)-2-(hexadecanoylamino)-1-[(4,6-O-benzylidene-β-D-galactopyranosyl)oxy]-4-octadecene 

Relevant articles and documents

Sulfated galactocerebrosides as potential antiinflammatory agents

Native sulfatides, as well as many sulfated glycolipids, have been shown to avidly bind to the selectin receptors. In vivo, native sulfatides significantly block activity in selectin-dependent inflammatory responses. The fact that nonsulfated galactocerebrosides did not inhibit selectin- mediated adhesion identified a critical role for the anionic sulfate residue. We therefore initiated a program to evaluate the activity of position isomers. This study showed a binding selectivity for the positions 2 and 3 of the sulfate group on the carbohydrate ring as well as enhanced activity for the disulfated analogs. Furthermore, it was discovered that the attachment of lipophilic substituents on the carbohydrate ring was tolerated, consistent with the presence of a lipophilic pocket in the binding cavity. This resulted in compounds with a 6-fold increased potency.