202824-35-9

Upstream product

• 119471-50-0 phrnacyl (R)-3-hydroxydecanoate 
• 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 
• 128962-63-0 ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside 
• 1214-98-8 phenyl 1-thio-α-L-rhamnopyranose 
• 127753-94-0 ethyl 1-thio-α-L-rhamnopyranoside 
• 202824-31-5 ethyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-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 

Downstream Products

• 125135-03-7 rhamnolipid 
• 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 
• 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 

Relevant academic research and scientific papers

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.