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PMR configurational analysis of pinitol with the aid of lanthanide shift reagents and the homonuclear INDOR technique

✍ Scribed by F. Cavagna; A. Groebel

Publisher: John Wiley and Sons
Year: 1973
Tongue: English
Weight: 237 KB
Volume: 5
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270050306

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✦ Synopsis

Abstract

The PMR spectrum of the peracetylated O‐methyl‐chiro‐inositol (pinitol) could be analysed by employing lanthanide shift reagents and performing spin‐decoupling and INDOR experiments. The 100 MHz theoretical spectrum has been simulated and good agreement with the experiment has been achieved. Analysis of the vicinal HH‐couplings yields the relative configuration.

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An assignment of relative configurations has been achieved for the diastereomeric racernates(lR2R,lS2S) and (1R2S, 1S2R) of 3,3-dimethyl-l,2-diphenylbuta~-l-ol through the comparative analysis of the respective chemical shifts induced by Eu(fod), in the 'H and '"C NMR spectra, and the corresponding