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An improved method for [5′‐ 2 H]‐labelling 3′‐ O ‐acetylthymidine
Author(s) -
Orban John,
Reid Brian R.
Publication year - 1989
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.2580270210
Subject(s) - swern oxidation , chemistry , labelling , yield (engineering) , deuterium , aldehyde , nuclear magnetic resonance spectroscopy , sodium , chromatography , organic chemistry , catalysis , dimethyl sulfoxide , biochemistry , materials science , physics , quantum mechanics , metallurgy
3′‐ O ‐Acetylthymidine ( 1 ) was converted to the β‐acetoxy aldehyde ( 3 ) using a modified Swern oxidation procedure. The crude product was reduced with sodium borodeuteride to give, after chromatography, [5′‐ 2 H]‐3′‐ O ‐acetylthymidine ( 4 ) in 68% overall yield from 1 . The extent of deuterium incorporation was >95% as judged by 1 H NMR spectroscopy.