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Synthesis of 4‐0‐(4,6‐di[ 14 C]ethylidene‐α‐D‐glucopyranosyl)‐4′‐demethyl‐4‐epipodophyllotoxin
Author(s) -
Haynes U. J.,
Swigor J. E.
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.2580281110
Subject(s) - chemistry , yield (engineering) , acetic acid , stereochemistry , organic chemistry , metallurgy , materials science
The synthesis of the title compound ( 5 ) is described. Protection of 4‐0‐(4, 6‐ethylidene‐α‐D‐glucopyranosyl)‐4′‐demethyl‐4‐epipodophyllotoxin ( 1 ) with benzylchloroformate in the presence of pyridine gave 4‐0‐(4, 6‐ethylidene‐α‐D‐glucopyranosyl)‐4′‐carbobenzyloxy‐4‐epipodophyllotoxin ( 2 ). Treatment of ( 2 ) with acetic acid‐water produced 4‐0‐(α‐D‐glucopyranosyl)‐4′‐carbobenzyloxy‐4‐epipodophyllotoxin ( 3 ). Reaction of [ 14 C]acetaldehyde diethylacetal with ( 3 ) introduced the label in the 4′,6′‐ethylidene position ( 4 ). Hydrogenation using 30% palladium on carbon yielded the title compound ( 5 ) in an overall yield of 6%.