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Die Konstitution der isomeren Acetyldigitoxine. 48. Mitteilung über Herzglykoside
Author(s) -
Kuhn Max,
Lichti Heinz,
von Wartburg Albert
Publication year - 1962
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19620450318
Subject(s) - chemistry , phenylisocyanate , stereochemistry , medicinal chemistry
The reaction with phenylisocyanate transformed both acetyldigitoxin‐α and acetyldigitoxin‐β into their tris‐phenylurethanes (I and IX, respectively). By degradation of these derivatives, the constitutions of the degluco‐lanatosides could be elucidated. In acetyldigitoxin‐α, the characteristic acetyl group is attached to C‐3 of the terminal digitoxose unit, while the acetyl group of acetyldigitoxin‐β is located at C‐4 of the terminal sugar. The reversible rearrangement of the isomeric acetyl‐digitoxins represents an acyl migration.

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