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Strukturelle Abwandlungen am Vitamin D 3 . 3. Mitteilung [1]. Synthese und eigenschaften von SO 2 ‐addukten des (5 Z )‐ und (5 E )‐vitamins D 3
Author(s) -
Reischl Wolfgang,
Zbiral Erich
Publication year - 1979
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.19790620609
Subject(s) - chemistry , adduct , sulfur dioxide , vitamin , sulfur , medicinal chemistry , stereochemistry , inorganic chemistry , organic chemistry , biochemistry
Structural Modifications of Vitamin D 3 . Synthesis and Properties of the SO 2 ‐Adducts with (5 Z )‐ and (5 E )‐Vitamin D 3 Treatment of (5 Z )‐ and (5 E )‐vitamin D 3 ( 4 ) with sulfur dioxide yields each quantitatively the cyclic sulfones 1a and 1b . Thermally induced elimination of sulfur dioxide leads to either isotachysterol 3 ( 3 ) alone or mixtures of isotachysterol 3 ( 3 ) and isovitamin D 3 ( 2 ). On the other hand the extrusion of SO 2 can be brought about by means of KOH/CH 3 OH or on an alumina surface affording (5 E )‐vitamin D 3 ( 4 ). On treatment with CD 3 UD/ t BuOK/D 2 O 1a and 1b are transformed (5 E )‐6, 19, 19′‐trideuteriovitamin D 3 ( 4a ).