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Letters in Organic Chemistry

Author(s): János Marton*, Paul Cumming, Beate Bauer and Gjermund Henriksen*

DOI: 10.2174/1570178617999200719153812

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A New Precursor for the Radiosynthesis of 6-O-(2-[18F]Fluoroethyl)-6-Odesmethyl- diprenorphine ([18F]FE-DPN) by Nucleophilic Radiofluorination

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Abstract

We present the preparation of the new precursor 6-O-(2-tosyloxyethoxy)-6-O-desmethyl-3- O-trityl-diprenorphine (TE-TDDPN) for a one-pot, two-step nucleophilic radiosynthesis of 6-O-(2- [18F]fluoroethyl-6-O-desmethyl-diprenorphine ([18F]FE-DPN). The route to the precursor consists of a five-step synthesis starting from diprenorphine. We also provide alternative synthesis routes for the cold reference standard and the complete 1H- and 13C-NMR assignment of the prepared derivatives.

Keywords: Fluoroethyl-diprenorphine, opioid receptors, positron emission tomography, orvinols, PET-precursor, 6, 14- ethenomorphinans.

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