122911-24-4

Basic information

• Product Name: 3-[(3-{[6-deoxy-2-O-(6-deoxy-alpha-L-mannopyranosyl)-L-mannopyranosyl]oxy}decanoyl)oxy]decanoic acid
• CAS NO: 122911-24-4
• Molecular Formula: C₃₂H₅₈O₁₃
• Molecular Weight: 650.7951
• Mol File: 122911-24-4.mol

Chemical Properties

• Boiling Point: 798.8°C at 760 mmHg
• Flash Point: 243.4°C
• Density: 1.23g/cm³
• Vapor Pressure: 1.65E-29mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: 3-[(3-{[6-deoxy-2-O-(6-deoxy-alpha-L-mannopyranosyl)-L-mannopyranosyl]oxy}decanoyl)oxy]decanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(3-{[6-deoxy-2-O-(6-deoxy-alpha-L-mannopyranosyl)-L-mannopyranosyl]oxy}decanoyl)oxy]decanoic acid(122911-24-4)
• EPA Substance Registry System: 3-[(3-{[6-deoxy-2-O-(6-deoxy-alpha-L-mannopyranosyl)-L-mannopyranosyl]oxy}decanoyl)oxy]decanoic acid(122911-24-4)

Safety Data

• Hazardous Substances Data: 122911-24-4(Hazardous Substances Data)

Upstream product

• 57-48-7 D-Fructose 
• 56-81-5 glycerol 
• 202824-37-1 (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxy-(R)-decanoic acid 
• 127753-94-0 ethyl 1-thio-α-L-rhamnopyranoside 
• 202824-32-6 phenyl (2'R,3'R)-3,4-O-2',3'-dimethoxybutane-2',3'-diyl-1-thio-α-L-rhamnopyranoside 
• 202824-33-7 (R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester 
• 202824-36-0 (R)-3-{(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoyl}oxydecanoic acid 
• 56618-58-7 methyl (R)-3-hydroxydecanoate 
• 202824-35-9 C₆₇H₉₂O₁₆ 
• 1055030-00-6 (R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoic acid 
• 202824-31-5 ethyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-α-L-rhamnopyranoside 
• 1214-98-8 phenyl 1-thio-α-L-rhamnopyranose 
• 128962-63-0 ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside 

Relevant articles and documents

Synthesis of α-1,2- and α-1,3-linked di-rhamnolipids for biological studies

For a detailed examination of the interaction of rhamnose containing derivatives with recombinant horseshoe crab plasma lectin (rHPL), two di-rhamno-di-lipids (an α-1,2- and an α-1,3-linked) were synthesized via a new simple method. The N-iodosuccinimide/triflic acid mediated glycosylation of the methyl (R)-3-hydroxydecanoate with phenyl-1-thio-rhamnobioside donors afforded the mono-lipid disaccharides. Removal of the methyl ester group followed by esterification of the mono-lipids with a second (R)-3-hydroxydecanoate unit resulted in fully protected di-lipid derivatives, transformation of which into the target compounds was accomplished in two steps. This method allows the synthesis of both regioisomers in only 6 steps starting from the corresponding free disaccharides. Both synthetic di-rhamnolipids were biologically active for lectin binding differential binding preference between two isomeric di-rhamno-di-lipids. The rHPL lectin favours the α-1,3-linked di-rhamno-di-lipids over its α-1,2-linked regioisomer.

An efficient synthesis of (R)-3-{(R)-3-[2-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl] oxydecanoyl}oxydecanoic acid, a rhamnolipid from Pseudomonas aeruginosa

N-iodosuccinmide/triflic acid mediated one-pot two-step glycosylation of ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamnopyranoside (8) with phenyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-α-L-rhamnopyranoside (10b) and phenacyl (R)-3-hydroxydecanoate (13) gave rhainnolipid 17. The latter was transformed in five steps into the title compound 2. Esterification of 2 with diazomethane resulted into the corresponding methyl ester derivative 1.