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Synlett 2000; 2000(5): 0716-0718
DOI: 10.1055/s-2000-6593
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Synthesis of N-Phosphorylsulfamates (as Pyrophosphate and Carbamylphosphate Analogues) through an Imidate-Amidate Rearrangement

Sihem Boudjabi* , Georges Dewynter, Jean-Louis Montero
  • *Laboratoire de Chimie Biomoléculaire, UMR 5032. CC 073, Université Montpellier-II. Place E. Bataillon, 34095 Montepellier, France; Fax (33)467 144 824; E-mail: dewynter@crit.univ-montp2.fr
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Publication Date:
31 December 2000 (online)

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The sulfamates R-X-SO2-NH2 (X = O, NH) derived from amino acids or n-octanol react easily with trialkylphosphites in the presence of diisopropylazodicarboxylate (DIAD) to give phospha-λ 5-azenes R-X-SO2-N = P(OR′)3. Under basic conditions (DABCO), these derivatives are isomerized with loss of an alkyl group to N-phosphorylsulfamates R-X-SO2-NH-PO (OR′)2. Such structure can be regarded as a bioisoster of pyrophosphate or carbamoylphosphate.

phosphaazenes - pyrophosphate - amidate-imidate rearrangement - carbamoylphosphate