5alpha-Androstane-3beta,17beta-diol → HCID 22801525, compound

HRID 1834995

Reaction equation

HRID 1834995 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@@H:7]([CH2:8][CH2:9][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].[OH:30][CH2:31][C@@:32]12[C@@H:49]3[C@H:40]([C@H:41]4[C@@:45]([CH2:47][CH2:48]3)([CH3:46])[C:44](=[O:50])[CH2:43][CH2:42]4)[CH2:39][CH2:38][C@H:37]1[CH2:36][C@@H:35]([O:51][Si:52]([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH2:34][CH2:33]2.[OH:71][C@H:72]1CC[C@@]2(C=O)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2O)C1.[CH3:93][C@]12CC[C@H]3[C@@H](CC[C@@H]4[C@]3(C)CC[C@H](O)C4)[C@@H]1CC[C@@H]2O>>[C:1]([O:4][C@H:5]1[CH2:22][C@@H:21]([CH3:23])[C@@:20]2([CH2:24][O:25][CH3:31])[C@@H:7]([CH2:8][CH2:9][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].[CH3:23][C@:21]1([O:71][CH3:72])[CH2:22][CH2:6][C@H:7]2[C@H:8]3[C@H:9]([CH2:10][CH2:19][C@:20]12[CH3:24])[C@:45]1([CH2:44][O:50][CH3:93])[C@H:41]([CH2:40][CH2:49][CH2:48][CH2:47]1)[CH2:42][CH2:43]3.[CH3:1][O:30][CH2:31][C@@:32]12[C@@H:49]3[C@H:40]([C@H:41]4[C@@:45]([CH2:47][CH2:48]3)([CH3:46])[C:44](=[O:50])[CH2:43][CH2:42]4)[CH2:39][CH2:38][C@H:37]1[CH2:36][C@@H:35]([O:51][Si:52]([C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)([C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)[C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1)[CH2:34][CH2:33]2.[CH3:1][O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH:24]=[O:25])[C@@H:7]([CH2:8][CH2:9][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][CH3:27])[CH2:6]1

Participants

8

Reactant 4

HCID 2423325alpha-Androstane-3beta,17beta-diolHCID 21626207HCID 21626207, compoundHCID 22801524HCID 22801524, compoundHCID 706146361beta-Methyl-5alpha-androstane-3beta,17beta,19-triol 3,17-diacetate

Product 4

HCID 22801525HCID 22801525, compoundHCID 70614924HCID 70614924, compoundHCID 8673543719-Methoxy-1beta-methyl-5alpha-androstane-3beta,17beta-diol diacetateHCID 88801553HCID 88801553, compound

Procedure

Substituting 1β-methyl-5α-androstane-3β,17β,19-triol 3,17-diacetate, 17α-methyl-5α-androstane-17β,19-diol, 19-hydroxy-3β-triphenylsiloxy-5α-androstan-17-one and 3β,17β-dihydroxy-5α-androstan-19-one for the 1β-methyl-19-2'-tetrahydropyranyloxy)-5α-androstane-3β,17β-diol above results in the preparation of 19-methoxy-1β-methyl-5α-androstane-3β,17β-diol diacetate, 17α-methyl-17β,19-dimethoxy-5α-androstane, 19-methoxy-3β-triphenylsiloxy-5α-androstan-17-one and 3β,17β-dimethoxy-5α-androstan-19-one, respectively.

Sources & evidence

ORD record
ord-5bca20f9fe4f44d59fc34d938ecfbcaa
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Linked notes

Loading…