A facile permethylation of cord factor.
Small quantities of cord factor (trehalose-6,6'-dimycolates) can be readily and almost quantitatively permethylated in anhydrous diethyl ether/dimethylformamide mixtures with CH3I and NaH-oil dispersion in the presence of molecular sieve. Hydrolysis of the permethylated products from cord factor "Peurois" and 'P3-Aoyama-b' prove these to be 6,6'-dimycolates. Experiments with a 4-palmitoyl glucose suggest that acyl migration in this system may not occur.
D055598:Chemical Phenomena; D002621:Chemistry; D002845:Chromatography; D003311:Cord Factors / Q000138:chemical synthesis*; D006017:Glycolipids / Q000138:chemical synthesis*; D008722:Methods; D008745:Methylation
D003311:Cord Factors; D006017:Glycolipids