Reaction SMILES: C([O:4][CH2:5][C@@:6]12[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([O:24][Si:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]1=[CH:10][C@@H:9]([O:44][Si:45]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:8][C@H:7]2[CH3:64])(=O)C.C([O:68][CH2:69][C@@:70]12[C@@H:87]3[C@H:78]([C@H:79]4[C@@:83]([CH2:85][CH2:86]3)([CH3:84])[C@@H:82]([O:88][Si:89]([C:102]3[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=3)([C:96]3[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=3)[C:90]3[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=3)[CH2:81][CH2:80]4)[CH2:77][C@H:76]([CH3:108])[C:75]1=[CH:74][C@@H:73]([O:109][Si:110]([C:123]1[CH:128]=[CH:127][CH:126]=[CH:125][CH:124]=1)([C:117]1[CH:122]=[CH:121][CH:120]=[CH:119][CH:118]=1)[C:111]1[CH:116]=[CH:115][CH:114]=[CH:113][CH:112]=1)[CH2:72][CH2:71]2)(=O)C.C(OC[C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)[C@@H](O[Si](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)CC4)CCC1=C[C@@H](O[Si](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CC2)(=O)C>>[CH3:64][C@H:7]1[C@@:6]2([CH2:5][OH:4])[C:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[O:24][Si:25]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:10][C@@H:9]([O:44][Si:45]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH2:8]1.[CH3:108][C@@H:76]1[C:75]2[C@:70]([CH2:69][OH:68])([CH2:71][CH2:72][C@H:73]([O:109][Si:110]([C:117]3[CH:118]=[CH:119][CH:120]=[CH:121][CH:122]=3)([C:111]3[CH:116]=[CH:115][CH:114]=[CH:113][CH:112]=3)[C:123]3[CH:128]=[CH:127][CH:126]=[CH:125][CH:124]=3)[CH:74]=2)[C@@H:87]2[C@H:78]([C@H:79]3[C@@:83]([CH2:85][CH2:86]2)([CH3:84])[C@@H:82]([O:88][Si:89]([C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)([C:102]2[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=2)[C:96]2[CH:97]=[CH:98][CH:99]=[CH:100][CH:101]=2)[CH2:81][CH2:80]3)[CH2:77]1
Reactant: CC(=O)OC[C@]12CC[C@H](O[Si](c3ccccc3)(c3ccccc3)c3ccccc3)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](c3ccccc3)(c3ccccc3)c3ccccc3)CC[C@@H]12
Reactant: CC(=O)OC[C@@]12C(=C[C@@H](O[Si](c3ccccc3)(c3ccccc3)c3ccccc3)C[C@H]1C)CC[C@H]1[C@@H]3CC[C@H](O[Si](c4ccccc4)(c4ccccc4)c4ccccc4)[C@@]3(C)CC[C@@H]12
Agent: CC(=O)OC[C@]12CC[C@H](O[Si](c3ccccc3)(c3ccccc3)c3ccccc3)C=C1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](c3ccccc3)(c3ccccc3)c3ccccc3)CC[C@@H]12
Product: C[C@@H]1C[C@H](O[Si](c2ccccc2)(c2ccccc2)c2ccccc2)C=C2CC[C@H]3[C@@H]4CC[C@H](O[Si](c5ccccc5)(c5ccccc5)c5ccccc5)[C@@]4(C)CC[C@@H]3[C@]21CO
Product: C[C@H]1C[C@@H]2[C@H](CC[C@]3(C)[C@@H](O[Si](c4ccccc4)(c4ccccc4)c4ccccc4)CC[C@@H]23)[C@@]2(CO)CC[C@H](O[Si](c3ccccc3)(c3ccccc3)c3ccccc3)C=C12

Procedure:
Following the same procedure and substituting 1β-methyl-3β,17β-di-(triphenylsiloxy)-4-androsten-19-ol acetate and 6α-methyl-3β,17β-di-(triphenylsiloxy)-4-androsten-19-ol acetate for the 3β,17β-di-(triphenylsiloxy)androst-4-en-19-ol acetate above results in the preparation of 1β-methyl-3β,17β-di-(triphenylsiloxy)-4-androsten-19-ol and 6α-methyl-3β,17β-di-(triphenylsiloxy)-4-androsten-19-ol, respectively.