Synthesis of carboxylic acid glucuronides
AssigneeSynthetic Technology Corporation
InventorsMarcus A. Tius, Mark R. Hagadone
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Abstract
A method of producing a carboxylic acid glucuronide by reacting a carboxylic acid precursor with a blocked sugar epoxide precursor is disclosed. Also disclosed are: deuterated 11-nor-.DELTA..sup.8 - or .DELTA..sup.9 -THC carboxylic acid glucuronide having a deuterated hydrocarbon chain; 5'-deuterated 11-nor-.DELTA..sup.8 - or .DELTA..sup.9 -THC-carboxylic acid or 5'-deuterated .DELTA..sup.8 - or .DELTA..sup.9 -THC glucuronide. The compositions are useful as GC-MS standards; in methods for preparing antibodies reactive with a THC glucuronide; and, in GC-MS diagnostic methods for THC metabolites.
Claims5
A method of producing a carboxylic acid glucuronide comprising
- reacting a carboxylic acid precursor with a dual-blocked sugar epoxide precursor of the formula:
- ##STR4## wherein R.sub.6 is a first protective agent, and R.sub.7 and R.sub.8 are a second protective agent, to obtain a dual-blocked carboxylic acid glucuronide precursor;
- and then
- removing the first and the second protective agents from the dual-blocked sugar epoxide precursor to obtain a carboxylic acid glucuronide of the formula:
- ##STR5## wherein R.sub.13 is the acyl residue of said carboxylic acid precursor.
Dependencies are inferred from the claim text.