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

Sihem Boudjabi; Georges Dewynter; Jean-Louis Montero

doi:10.1055/s-2000-6593

Synlett 2000; 2000(5): 0716-0718
DOI: 10.1055/s-2000-6593

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

PDF Download All articles of this category

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

PDF (54 kb)