Reaktion #1477954

ord-86950ed2e3264be7af1ea97fded63bfb

Reaktionsgleichung

CC(C)(C)[Si](C)(C)OC[C@]12CCC(=O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-t-butyldimethylsiloxy-5-androstene-3,17-dione
C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@@]43CO)[C@@H]1CC[C@@H]2O
17β,19-dihydroxy-5-androsten-3-one
→
CC(C)(C)[Si](C)(C)OC[C@]12CC[C@@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(O)CC[C@@H]12
19-t-butyldimethylsiloxy-5-androstene-3α,17-diol

Edukte

—
1β-methyl-19-(4'-tetrahydropyranyloxy)-5-androstene-3,17-dione
CC(C)(C)[Si](C)(C)OC[C@]12CCC(=O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-t-butyldimethylsiloxy-5-androstene-3,17-dione
C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@@]43CO)[C@@H]1CC[C@@H]2O
17β,19-dihydroxy-5-androsten-3-one
—
4α-methyl-17β,19-di(4'-tetrahydropyranyloxy)-5-androsten-3-one

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Substituting 19-t-butyldimethylsiloxy-5-androstene-3,17-dione, 4α-methyl-17β,19-di(4'-tetrahydropyranyloxy)-5-androsten-3-one and 1β-methyl-19-(4'-tetrahydropyranyloxy)-5-androstene-3,17-dione for the 17β,19-dihydroxy-5-androsten-3-one above results in the preparation of 19-t-butyldimethylsiloxy-5-androstene-3α,17-diol, 4α-methyl-17β,19-di(4'-tetrahydropyranyloxy)-5-androsten-3α-ol and 1β-methyl-19-(4'-tetrahydropyranyloxy)-5-androstene-3α,17β-diol, respectively.

Quelle

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