3beta,17beta,19-Tri(trimethylsiloxy)androst-4-ene → 1alpha-Methyl-17beta,19-di(trimethylsiloxy)androst-4-ene

HRID 1733072Notes

Reaction equation

HRID 1733072 reaction equation
[CH3:1][C@@H:2]1[C@@:19]2([CH2:20][OH:21])[C:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[OH:22])=[CH:5][CH2:4][CH2:3]1.[CH3:23][C@@H]1[C@@]2(CO)C(CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2O)=C[C@@H](O)C1.[CH3:46][C@@H]1CC2[C@](CO)(CC[C@H](O)C=2)[C@@H]2[C@@H]1[C@H]1[C@@](CC2)(C)[C@@H](O)CC1.[CH3:69][Si:70]([CH3:102])([CH3:101])[O:71][C@H:72]1[CH2:89][CH2:88][C@@:87]2([CH2:90][O:91][Si:92]([CH3:95])([CH3:94])[CH3:93])[C:74]([CH2:75][CH2:76][C@@H:77]3[C@@H:86]2[CH2:85][CH2:84][C@@:82]2([CH3:83])[C@H:78]3[CH2:79][CH2:80][C@@H:81]2[O:96][Si:97]([CH3:100])([CH3:99])[CH3:98])=[CH:73]1>>[CH3:1][C@@H:2]1[C@@:19]2([CH2:20][O:21][Si:70]([CH3:102])([CH3:101])[CH3:69])[C:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[O:22][Si:70]([CH3:102])([CH3:101])[CH3:69])=[CH:5][CH2:4][CH2:3]1.[CH3:23][C@@H:88]1[C@@:87]2([CH2:90][O:91][Si:92]([CH3:95])([CH3:94])[CH3:93])[C:74]([CH2:75][CH2:76][C@@H:77]3[C@@H:86]2[CH2:85][CH2:84][C@@:82]2([CH3:83])[C@H:78]3[CH2:79][CH2:80][C@@H:81]2[O:96][Si:97]([CH3:100])([CH3:99])[CH3:98])=[CH:73][C@@H:72]([O:71][Si:70]([CH3:101])([CH3:69])[CH3:102])[CH2:89]1.[CH3:46][C@@H:76]1[CH2:75][C:74]2[C@:87]([CH2:90][O:91][Si:92]([CH3:95])([CH3:94])[CH3:93])([CH2:88][CH2:89][C@H:72]([O:71][Si:70]([CH3:101])([CH3:69])[CH3:102])[CH:73]=2)[C@@H:86]2[C@@H:77]1[C@H:78]1[C@@:82]([CH2:84][CH2:85]2)([CH3:83])[C@@H:81]([O:96][Si:97]([CH3:100])([CH3:99])[CH3:98])[CH2:80][CH2:79]1

Participants

7

Reactant 4

HCID 228032683beta,17beta,19-Tri(trimethylsiloxy)androst-4-eneHCID 705847581alpha-Methyl-4-androstene-17beta,19-diolHCID 705849827alpha-Methyl-4-androstene-3beta,17beta,19-triolHCID 705863741alpha-Methyl-4-androstene-3beta,17beta,19-triol

Product 3

HCID 228032621alpha-Methyl-17beta,19-di(trimethylsiloxy)androst-4-eneHCID 228032631alpha-Methyl-3beta,17beta,19-tri(trimethylsiloxy)androst-4-eneHCID 228032767alpha-Methyl-3beta,17beta,19-tri(trimethylsiloxy)-4-androstene

Procedure

Following essentially the same procedure but substituting 1α-methyl-4-androstene-17β,19-diol, 1α-methyl-4-androstene-3β,17β,19-triol and 7α-methyl-4-androstene-3β,17β,19-triol for the androst-4-ene-3β,17β,19-triol above results in the formation of 1α-methyl-17β,19-di(trimethylsiloxy)androst-4-ene, 1α-methyl-3β,17β,19-tri(trimethylsiloxy)androst-4-ene and 7α-methyl-3β,17β,19-tri(trimethylsiloxy)-4-androstene, respectively.

Sources & evidence

ORD record
ord-b8560131081646aba9508822ef0e156d
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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