Reagents for stereoselective preparation of N-carbamyl β-D-glucuronides.
2011
Carbamyl glucuronidation is an increasingly well-recognized route of metabolism for secondary amine drugs. Proper characterization of these metabolites requires the synthesis of authentic standards. O-Protected glucuronyl p-nitrophenyl carbonates can be prepared with high selectivity for the β-configuration at the anomeric center and efficiently transfer the β-glucuronylcarbonyl group to secondary amines, constituting an effective and versatile method for preparation of these metabolites.
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