3beta,17beta-Di(triphenylsiloxy)-5-androsten-19-ol → 3beta,17beta-Di(triphenylsiloxy)-5-androsten-19-one

HRID 1390785Notes

Reaction equation

HRID 1390785 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH:9]=[C:8]1[CH2:7][C:6](=[O:22])[CH2:5][C@@H:4]2[CH3:23].[C:24]1([Si:30]([C:78]2[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=2)([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[O:31][C@H:32]2[CH2:49][CH2:48][C@@:47]3([CH2:50][OH:51])[C:34](=[CH:35][CH2:36][C@@H:37]4[C@@H:46]3[CH2:45][CH2:44][C@@:42]3([CH3:43])[C@H:38]4[CH2:39][CH2:40][C@@H:41]3[O:52][Si:53]([C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:33]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH3:23][C@@H:4]1[C@@:3]2([CH:2]=[O:1])[C:8](=[CH:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:21])[CH2:7][C:6](=[O:22])[CH2:5]1.[C:78]1([Si:30]([C:72]2[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:31][C@H:32]2[CH2:49][CH2:48][C@@:47]3([CH:50]=[O:51])[C:34](=[CH:35][CH2:36][C@@H:37]4[C@@H:46]3[CH2:45][CH2:44][C@@:42]3([CH3:43])[C@H:38]4[CH2:39][CH2:40][C@@H:41]3[O:52][Si:53]([C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)([C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[C:66]3[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=3)[CH2:33]2)[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1

Participants

4

Reactant 2

HCID 228069173beta,17beta-Di(triphenylsiloxy)-5-androsten-19-olHCID 7060533419-Hydroxy-1alpha-methyl-5-androstene-3,17-dione

Product 2

HCID 228069183beta,17beta-Di(triphenylsiloxy)-5-androsten-19-oneHCID 867363261alpha-Methyl-5-androstene-3,17,19-trione

Procedure

Substituting 17β,19-dihydroxy-1α,17α-dimethyl-5-androsten-3-one, 19-hydroxy-1α-methyl-5-androstene-3,17-dione, 17β,19-dihydroxy-4α,6,17α-trimethyl-5-androsten-3-one, 17β-(2'-tetrahydropyranyloxy)-5-androsten-19-ol and 3β,17β-di(triphenylsiloxy)-5-androsten-19-ol for the 17α-methyl-5-androstene-3β,17β,19-triol 3,17-diacetate above results in the preparation of 17β-hydroxy-1α,17α-dimethyl-5-androstene-3,19-dione, 1α-methyl-5-androstene-3,17,19-trione, 17β-hydroxy-4α,6,17α-trimethyl-5-androstene-3,19-dione, 17β-(2'-tetrahydropyranyloxy)-5-androsten-19-one and 3β,17β-di(triphenylsiloxy)-5-androsten-19-one, respectively.

Sources & evidence

ORD record
ord-a764a32c9b81455f8565c8c92a625dd7
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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