19-Trimethylsiloxy-5alpha-androstane-3beta,17beta-diol → 17beta-Trimethylsiloxy-5alpha-androstane-3,19-dione

HRID 1834971Notes

Reaction equation

HRID 1834971 reaction equation
[CH3:1][Si:2]([CH3:26])([CH3:25])[O:3][C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:21]([CH2:22][CH2:23][C@:5]12[CH3:6])[C@:18]1([CH2:19][OH:20])[C@H:13]([CH2:14][C@@H:15]([OH:24])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3.[C:27]1([Si:33]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[O:34][C@H:35]2[CH2:52][CH2:51][C@@:50]3([CH2:53][OH:54])[C@@H:37]([CH2:38][CH2:39][C@@H:40]4[C@@H:49]3[CH2:48][CH2:47][C@@:45]3([CH3:46])[C@H:41]4[CH2:42][CH2:43][CH:44]3[OH:55])[CH2:36]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C[Si](C)(C)OC[C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)[C@@H](O)CC4)CC[C@H]1C[C@@H](O)CC2>>[CH3:25][Si:2]([CH3:1])([CH3:26])[O:3][C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:21]([CH2:22][CH2:23][C@:5]12[CH3:6])[C@:18]1([CH:19]=[O:20])[C@H:13]([CH2:14][C:15](=[O:24])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3.[C:56]1([Si:33]([C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:34][C@H:35]2[CH2:52][CH2:51][C@@:50]3([CH:53]=[O:54])[C@@H:37]([CH2:38][CH2:39][C@@H:40]4[C@@H:49]3[CH2:48][CH2:47][C@@:45]3([CH3:46])[C@H:41]4[CH2:42][CH2:43][C:44]3=[O:55])[CH2:36]2)[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Participants

5

Reactant 3

HCID 2280149619-Trimethylsiloxy-5alpha-androstane-3beta,17beta-diolHCID 2280152117beta-Trimethylsiloxy-5alpha-androstane-3beta,19-diolHCID 228015373beta-Triphenylsiloxy-5alpha-androstane-17,19-diol

Product 2

HCID 2280152017beta-Trimethylsiloxy-5alpha-androstane-3,19-dioneHCID 228015383beta-Triphenylsiloxy-5alpha-androstane-17,19-dione

Procedure

Substituting 17β-trimethylsiloxy-5α-androstane-3β,19-diol and 3β-triphenylsiloxy-5α-androstane-17,19-diol for the 19-trimethylsiloxy-5α-androstane-3β,17β-diol above results in the preparation of 17β-trimethylsiloxy-5α-androstane-3,19-dione and 3β-triphenylsiloxy-5α-androstane-17,19-dione.

Sources & evidence

ORD record
ord-0114b532ca734136ba4d8104a727a7e8
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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