Reaktion #1477944

ord-12d0610f3e91445797e01c550da55ffb

Reaktionsgleichung

COC[C@]12C(=CC[C@@H]3[C@@H]1CC[C@]1(C)C(=O)CC[C@@H]31)CC(=O)C[C@H]2C
19-methoxy-1β-methyl-5-androstene-3,17-dione
COC[C@]12CCC(=O)CC1=C(C)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-methoxy-6-methyl-5-androsten-3,17-dione
COC[C@]12CCC(=O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-methoxyandrost-5-ene-3,17-dione
→
COC[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
19-methoxyandrost-5-ene-3β,17β-diol
COC[C@]12CC[C@H](O)CC1=C(C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
19-methoxy-6-methyl-5-androsten-3β,17β-diol
COC[C@]12C(=CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]31)C[C@@H](O)C[C@H]2C
19-methoxy-1β-methyl-5-androstene-3β,17β-diol

Edukte

—
6α,17α-dimethyl-17β,19-di(trimethylsiloxy)-5-androsten-3-one
COC[C@]12C(=CC[C@@H]3[C@@H]1CC[C@]1(C)C(=O)CC[C@@H]31)CC(=O)C[C@H]2C
19-methoxy-1β-methyl-5-androstene-3,17-dione
COC[C@]12CCC(=O)CC1=C(C)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-methoxy-6-methyl-5-androsten-3,17-dione
—
17α-propynyl-17β,19-di(trimethylsiloxy)-5-androsten-3β-ol
COC[C@]12CCC(=O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-methoxyandrost-5-ene-3,17-dione

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Substituting 6α,17α-dimethyl-17β,19-di(trimethylsiloxy)-5-androsten-3-one, 19-methoxyandrost-5-ene-3,17-dione, 19-methoxy-1β-methyl-5-androstene-3,17-dione and 19-methoxy-6-methyl-5-androsten-3,17-dione for the 17α-propynyl-17β,19-di(trimethylsiloxy)-5-androsten-3β-ol above results in the preparation of 6α,17α-dimethyl-17β,19-di(trimethylsiloxy)-5-androsten-3β-ol, 19-methoxyandrost-5-ene-3β,17β-diol, 19-methoxy-1β-methyl-5-androstene-3β,17β-diol and 19-methoxy-6-methyl-5-androsten-3β,17β-diol, respectively.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04139617uspto-grants-1979_02