Synthesis ofN-Phosphorylsulfamates (as Pyrophosphate and Carbamylphosphate Analogues) through an Imidate-Amidate Rearrangement

Abstract

The sulfamates R-X-SO 2 -NH 2 (X = O, NH) derived from amino acids or n-octanol react easily with trialkylphosphites in the presence of diisopropylazodicarboxylate (DIAD) to give phospha-l 5 -azenes R-X-SO 2 -N = P(OR') 3 . Under basic conditions (DABCO), these derivatives are isomerized with loss of an alkyl group to N-phosphorylsulfamates R-X-SO 2 -NH-PO (OR') 2 . Such structure can be regarded as a bioisoster of pyrophosphate or carbamoylphosphate.