1beta-Methyl-5-androstene-3beta,17beta,19-triol triacetate → 1beta,7alpha-Dimethyl-5alpha-androstane-3beta,17beta,19-triol 3,17-diacetate

HRID 1834983Notes

Reaction equation

HRID 1834983 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][C@@H:21]([CH3:23])[C@@:20]2([CH2:24][OH:25])[C:7](=[CH:8][C@@H:9]([CH3:30])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:26][C:27](=[O:29])[CH3:28])[CH2:6]1)(=[O:3])[CH3:2].[C:31]([O:34][C@H:35]1[CH2:52][C@@H:51]([CH3:53])[C@@:50]2([CH2:54][O:55][C:56](=[O:58])[CH3:57])[C:37](=[CH:38][CH2:39][C@@H:40]3[C@@H:49]2[CH2:48][CH2:47][C@@:45]2([CH3:46])[C@H:41]3[CH2:42][CH2:43][C@@H:44]2[O:59][C:60](=[O:62])[CH3:61])[CH2:36]1)(=[O:33])[CH3:32].[C:63]([O:66][C@H:67]1[CH2:84][C@@H:83]([CH3:85])[C@@:82]2([CH2:86][O:87][C:88](=[O:90])[CH3:89])[C:69](=[C:70]([CH3:95])[CH2:71][C@@H:72]3[C@@H:81]2[CH2:80][CH2:79][C@@:77]2([CH3:78])[C@H:73]3[CH2:74][CH2:75][C@@H:76]2[O:91][C:92](=[O:94])[CH3:93])[CH2:68]1)(=[O:65])[CH3:64].C(O[C@H]1C[C@@H](C)[C@@]2(CO)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2OC(=O)C)C1)(=O)C>>[C:1]([O:4][C@H:5]1[CH2:22][C@@H:21]([CH3:23])[C@@:20]2([CH2:24][OH:25])[C@@H:7]([CH2:8][C@@H:9]([CH3:30])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:26][C:27](=[O:29])[CH3:28])[CH2:6]1)(=[O:3])[CH3:2].[C:31]([O:34][C@H:35]1[CH2:52][C@@H:51]([CH3:53])[C@@:50]2([CH2:54][O:55][C:56](=[O:58])[CH3:57])[C@@H:37]([CH2:38][CH2:39][C@@H:40]3[C@@H:49]2[CH2:48][CH2:47][C@@:45]2([CH3:46])[C@H:41]3[CH2:42][CH2:43][C@@H:44]2[O:59][C:60](=[O:62])[CH3:61])[CH2:36]1)(=[O:33])[CH3:32].[C:63]([O:66][C@H:67]1[CH2:84][C@@H:83]([CH3:85])[C@@:82]2([CH2:86][O:87][C:88](=[O:90])[CH3:89])[C@@H:69]([C@H:70]([CH3:95])[CH2:71][C@@H:72]3[C@@H:81]2[CH2:80][CH2:79][C@@:77]2([CH3:78])[C@H:73]3[CH2:74][CH2:75][C@@H:76]2[O:91][C:92](=[O:94])[CH3:93])[CH2:68]1)(=[O:65])[CH3:64]

Participants

7

Reactant 4

HCID 706049301beta-Methyl-5-androstene-3beta,17beta,19-triol triacetateHCID 706145171beta,7alpha-Dimethyl-5-androstene-3beta,17beta,19-triol 3,17-diacetateHCID 706148731beta-Methyl-5-androstene-3beta,17beta,19-triol 3,17-diacetateHCID 706149551beta,6-Dimethyl-5-androstene-3beta,17beta,19-triol triacetate

Product 3

HCID 706145451beta,7alpha-Dimethyl-5alpha-androstane-3beta,17beta,19-triol 3,17-diacetateHCID 706147131beta,6beta-Dimethyl-5alpha-androstane-3beta,17beta,19-triol triacetateHCID 706151951beta-Methyl-5alpha-androstane-3beta,17beta,19-triol triacetate

Procedure

Substituting 1β,7α-dimethyl-5-androstene-3β,17β,19-triol 3,17-diacetate, 1β-methyl-5-androstene-3β,17β,19-triol triacetate and 1β,6-dimethyl-5-androstene-3β,17β,19-triol triacetate for the 1β-methyl-5-androstene-3β,17β,19-triol 3,17-diacetate above results in the preparation of 1β,7α-dimethyl-5α-androstane-3β,17β,19-triol 3,17-diacetate, 1β-methyl-5α-androstane-3β,17β,19-triol triacetate and 1β,6β-dimethyl-5α-androstane-3β,17β,19-triol triacetate, respectively.

Sources & evidence

ORD record
ord-a617a58d087e42f3b44a3ccf41e367f9
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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