Abstract
The product of
monotritylation of 3β,19-dihydroxyandrost-5-en-17-one is the 3β-trityl
ether, not the 19-trityl ether as previously proposed. In consequence the
product of acetylation of the monotrityl ether is 19-acetoxy-3β-trityloxyandrost-5-en-17-one
and thus acid-catalysed detritylation of this compound yields directly the
19-acetoxy derivative without the invoking of an acid-catalysed rearrangement.
The isomeric 3β-hydroxy-19-trityloxyandrost-5-en-17-one has been prepared
as well as a number of 3β-tritylated Δ5-steroids which
have been used to study the influence of the trityl ether group upon p.m.r.
chemical shifts in this series.
Cited by
4 articles.
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