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Synthesis of 4-0-(4,6-di[14C]ethylidene-α-D-glucopyranosyl)-4′-demethyl-4-epipodophyllotoxin

✍ Scribed by U. J. Haynes; J. E. Swigor

Book ID
102373856
Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
204 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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%.

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