Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst
for the acylation of alcohols with
acid anhydrides. Highly functionalized primary, secondary,
tertiary, and allylic alcohols, and
phenols, were acylated cleanly and efficiently and in a fraction of the
time used under the standard
DMAP conditions.
A novel receptor 4 has been prepared, which binds the monopotassium salts of various dicarboxylic acids in chloroform solution, using a combination of hydrogen bonding interactions and an electrostatic association between a carboxylate anion and a crown ether bound potassium cation, the crystal structure of the receptor is reported and evidence for the proposed binding interactions is provided by consideration of various extraction experiments, intermolecular NOES (nuclear Overhausser effect), and FAB (fast atom bombardment) mass spectrometry, where a bimolecular species, held together by hydrogen bonds, can be detected in the negative ion mass spectrum.
A series of novel pregnane derivatives bearing γ-butyrolactones at C21 were prepared and tested as glucocorticoid agonists. The compounds were also tested for their lability in human plasma, and found to be rapidly hydrolysed by the enzyme paraoxonase to the respective hydroxyacids.
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