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Synthesis of 4‐o‐(4,6‐ethylidene‐α‐D‐glucopyranosyl)‐4′‐demethyl‐3′‐O‐[ 14 C]methyl‐4‐epipodophyllotoxin
Author(s) -
Swigor J. E.,
Haynes U. J.
Publication year - 1990
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.2580280203
Subject(s) - chemistry , acetonitrile , yield (engineering) , sodium iodide , methyl iodide , palladium , iodide , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
The synthesis of the title compound (5) is described. Treatment of 4‐O‐(4,6‐ethylidene‐α‐D‐glucopyranosyl)‐4′‐demethyl‐4‐epipodophyllotoxin with sodium metaperiodate in acetonitrile formed the highly colored 4‐O‐(4,6‐ethylidene‐α‐D‐glucopyranosyl)‐3′,4′‐dioxo‐4‐epipodophyllotoxin (1). Hydrogenation using 10% palladium on carbon produced the 3′,4′‐dihydroxy compound (2). Protection of the 4′ hydroxy was achieved by benzylation (3). Treatment with excess [ 14 C]methyl iodide under basic conditions introduced the label on the 3′ position (4). Deprotection yielded the title compound in an overall yield of 6%.