Synthesis of new deuterium‐labelled lignanolactones | Zendy

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Synthesis of new deuterium‐labelled lignanolactones

Author(s) -

Leppälä Eija,

Pohjoispää Monika,

Koskimies Jorma,

Wähälä Kristiina

Publication year - 2008

Publication title -

journal of labelled compounds and radiopharmaceuticals

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.432

H-Index - 47

eISSN - 1099-1344

pISSN - 0362-4803

DOI - 10.1002/jlcr.1553

Subject(s) - chemistry , deuterium , reagent , hydrogen–deuterium exchange , medicinal chemistry , organic chemistry , hydrogen , physics , quantum mechanics

Deuteration of several lignanolactones, using 2 H 3 PO 4 ·BF 3 / 2 H 2 O as the deuteration reagent, is described, affording new stable isotopically pure polydeuterated lignans. All aromatic hydrogens are exchanged, including the less active ones. The order of 1 H/ 2 H exchange is studied by comparing calculated electrostatic potential values and experimental observations. Labile deuteriums are exchanged back to hydrogens with methanolic HCl to achieve stable isotopically pure compounds. Copyright © 2008 John Wiley & Sons, Ltd.

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