19-Hydroxy-3beta-triphenylsiloxy-5alpha-androstan-17-one acetate → 19-Hydroxy-3beta-triphenylsiloxy-5alpha-androstan-17-one
Reaction equation
C(O)(=O)C.[OH:5][CH2:6][C@@:7]12[C@@H:24]3[C@H:15]([C@H:16]4[C@@:20]([CH2:22][CH2:23]3)([CH3:21])[C:19](=[O:25])[CH2:18][CH2:17]4)[CH2:14][CH2:13][C@H:12]1[CH2:11][C@@H:10]([O:26][Si:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:9][CH2:8]2.C([O:49][C@H:50]1[CH2:67][C@@H:66]([CH3:68])[C@@:65]2([CH2:69][O:70][CH3:71])[C@@H:52]([CH2:53][CH2:54][C@@H:55]3[C@@H:64]2[CH2:63][CH2:62][C@@:60]2([CH3:61])[C@H:56]3[CH2:57][CH2:58][C@@H:59]2[O:72]C(=O)C)[CH2:51]1)(=O)C>>[OH:5][CH2:6][C@@:7]12[C@@H:24]3[C@H:15]([C@H:16]4[C@@:20]([CH2:22][CH2:23]3)([CH3:21])[C:19](=[O:25])[CH2:18][CH2:17]4)[CH2:14][CH2:13][C@H:12]1[CH2:11][C@@H:10]([O:26][Si:27]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:9][CH2:8]2.[CH3:71][O:70][CH2:69][C@@:65]12[C@@H:64]3[C@H:55]([C@H:56]4[C@@:60]([CH2:62][CH2:63]3)([CH3:61])[C@@H:59]([OH:72])[CH2:58][CH2:57]4)[CH2:54][CH2:53][C@H:52]1[CH2:51][C@@H:50]([OH:49])[CH2:67][C@H:66]2[CH3:68]Participants
4
Reactant 2
Product 2
Procedure
Substituting 3β-(1'-cyclopentenyloxy)-19-hydroxy-5α-androstan-17-one acetate, 19-hydroxy-3β-triphenylsiloxy-5α-androstan-17-one acetate and 19-methoxy-1β-methyl-5α-androstane-3β,17β-diol diacetate for the 19-hydroxy-3β-(2'-tetrahydropyranyloxy)-5α-androstan-17-one acetate above results in the preparation of 3β-(1'-cyclopentenyl-oxy)-19-hydroxy-5α-androstan-17-one, 19-hydroxy-3β-triphenylsiloxy-5α-androstan-17-one and 19-methoxy-1β-methyl-5α-androstane-3β,17β-diol, respectively.
Sources & evidence
- ORD record
- ord-f3c157dc37244076b72884d3750971d4
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04071625
Reaction notes
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