NMR Analysis of a Series of 6,14‐Ethenomorphinan Derivatives as PET Precursors and Reference Substances ** | Zendy

Marton János | Zendy; Sipos Attila | Zendy; Henriksen Gjermund | Zendy; Cumming Paul | Zendy; Berényi Sándor | Zendy; Schmitt Bettina M. | Zendy; Szabó Zoltán | Zendy

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NMR Analysis of a Series of 6,14‐Ethenomorphinan Derivatives as PET Precursors and Reference Substances **

Author(s) -

Marton János,

Sipos Attila,

Henriksen Gjermund,

Cumming Paul,

Berényi Sándor,

Schmitt Bettina M.,

Szabó Zoltán

Publication year - 2021

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.202101597

Subject(s) - desmethyl , chemistry , thebaine , regioselectivity , radiosynthesis , derivative (finance) , carbon 13 nmr , stereochemistry , combinatorial chemistry , organic chemistry , in vivo , medicine , biochemistry , codeine , microbiology and biotechnology , morphine , metabolite , financial economics , economics , pharmacology , biology , catalysis

The new semisynthetic oripavine derivative 3‐ O ‐trityl‐6‐ O ‐desmethyl‐dihydroetorphine was synthesized from the poppy alkaloid thebaine in a six‐step procedure. This compound can be applied as precursor for the radiosynthesis of [6‐ O ‐methyl‐ 11 C]‐dihydroetorphine ([ 11 C]DHE). We present a detailed description of 1 H and 13 C NMR data of reference standards and precursors for [6‐ O ‐methyl‐ 11 C]‐ and [6‐ O ‐(2‐[ 18 F]fluoroethyl]orvinols. This includes the complete assignment for 19 oripavine derivatives examined in 1D and 2D NMR experiments. We also investigated the molecular basis for regioselectivity of fluoroalkylation of 3‐ O ‐trityl‐6‐ O ‐desmethyl‐phenethyl‐orvinol (TDPEO) using computational methods.

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