USE OF 2D NMR FOR THE ASSIGNMENT OF STRUCTURE OF SOME DEFENCE RELATED COMPOUNDS

Authors
  1. Boulet, C.A.
  2. Tregear, S.J.
  3. Hansen, A.S.
Corporate Authors
Defence Research Establishment Suffield, Ralston ALTA (CAN)
Abstract
Organophosphorus nerve agents such as GA, GB, and GD, exist as mixtures of enantiomers. Studies by Benschop and co-workers (TNO) have shown substantial differences in activity between each enantiomer (and sets of diastereomers) of GD. However the synthesis, separation, and purification of the enantiomers of the G agents is laborious and impractical. Since we are interested in investigating the molecular mechanism of the reactivation of inhibited acetylcholinesterase by chiral Hagedorn oximes, a source of chiral phosphorus of known configuration was required. Reaction of a chiral amino alcohol with an alkyl phosphorodichloridate gives a mixture of diastereomers, epimeric at phosphorus, which can be separated by conventional chromatographic means. A seris of diastereotopic 1,3,2-oxazaphospholidine-2-ones were prepared from (plus) and (minus)-ephedrine. Analysis by 1D and 2D NMR has shown that it may be possible to establish the absolute configuration by NMR techniques. TRUNCATED
Report Number
DRES-SP-142-P-13 — @Paper presented at the NMR in Defence Sciences 1990 Symposium, Ralston, Alberta, Canada, 10-12 October 1990; CONTAINED IN 91-03239
Date of publication
15 May 1991
Number of Pages
12 (p13-24)
DSTKIM No
91-03237
CANDIS No
70428
Format(s):
Microfiche filmed at DSIS;Originator's fiche received by DSIS

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