The title compound has a structure containing three phenyl groups strung together end to end through their para positions with an n-pentyloxy cap at one terminal and a carboxylic acid function at the other. All three rings are therefore para disubstituted. This title acid, after coupling with the Echinocandin B macrocycle, gave a product with excellent pharmaceutical properties. The substructure compound, as an amide derivative, constitutes the drug Anidulafungin. Since this linkage would be broken during the drug’s metabolism and since the drug has been found to be safe, this would seem to establish that this acid component is fairly nontoxic in the human metabolism.
This compound is a moderately high melting solid and would be predicted to give high melting salts as well as covalent derivatives. For example, the esters and amides are more likely to be solids using this rather than other carboxyl coupling partners. The rigidity of the carbon skeleton might be expected to cause it to have a significant steric effect even remote to the point of attachment with another substructure. The expense of this potential protecting group would be ameliorated because the acid could be easily recovered and recrystallized to a dependable purity for recycling. Its use might be particularly promising where the process intermediates are expected to be liquids, oils, or waxes such as in prostaglandin synthesis.
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