5alpha-Androstane-3beta,17beta,19-triol → 3beta,17beta,19-Tri(triphenylsiloxy)-5alpha-androstane

HRID 1834968Notes

Reaction equation

HRID 1834968 reaction equation
[CH3:1][C@:2]12[CH2:20][CH2:19][C@H:18]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH2:16][OH:17])[CH2:14][CH2:13][C@H:12]([OH:21])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:22].C[C@@H:24]1[C@@:41]2([CH2:42][O:43][Si:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C@@H:28]([CH2:29][C@@H:30](C)[C@@H:31]3[C@@H:40]2[CH2:39][CH2:38][C@@:36]2([CH3:37])[C@H:32]3[CH2:33][CH2:34][C@@H:35]2[O:63][Si:64]([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH2:27][C:26](=[O:84])[CH2:25]1>>[C:51]1([Si:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[O:21][C@H:12]2[CH2:13][CH2:14][C@@:15]3([CH2:16][O:17][Si:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C@@H:10]([CH2:9][CH2:8][C@@H:7]4[C@@H:18]3[CH2:19][CH2:20][C@@:2]3([CH3:1])[C@H:6]4[CH2:5][CH2:4][C@@H:3]3[O:22][Si:64]([C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)([C:71]3[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=3)[C:77]3[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=3)[CH2:11]2)[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.[C:42]([OH:43])(=[O:17])[CH3:41].[OH:17][CH2:16][C@@:15]12[C@@H:18]3[C@H:7]([C@H:6]4[C@@:2]([CH2:20][CH2:19]3)([CH3:1])[C:3](=[O:22])[CH2:4][CH2:5]4)[CH2:8][CH2:9][C@H:10]1[CH2:11][C@@H:35]([O:63][Si:64]([C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)([C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[CH2:13][CH2:14]2.[C:16]([OH:17])(=[O:43])[CH3:15].[OH:84][CH:26]1[CH2:25][CH2:24][C@@:41]2([CH2:42][O:43][Si:44]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[C@@H:28]([CH2:29][CH2:30][C@@H:31]3[C@@H:40]2[CH2:39][CH2:38][C@@:36]2([CH3:37])[C@H:32]3[CH2:33][CH2:34][C:35]2=[O:63])[CH2:27]1

Participants

5

Reactant 2

HCID 158185065alpha-Androstane-3beta,17beta,19-triolHCID 228015301alpha,7alpha-Dimethyl-17beta,19-di(triphenylsiloxy)-5alpha-androstan-3-one

Product 3

HCID 228015343beta,17beta,19-Tri(triphenylsiloxy)-5alpha-androstaneHCID 8673543619-Hydroxy-3beta-triphenylsiloxy-5alpha-androstan-17-one acetateHCID 1317110263-Hydroxy-19-triphenylsiloxy-5alpha-androstan-17-one acetate

Procedure

Substituting 5α-androstane-3β,17β,19-triol, 3β,19-dihydroxy-5α-androstan-17-one 19-acetate and 3β,19-dihydroxy-5α-androstan-17-one 3-acetate for the 17β,19-dihydroxy-1α,7α-dimethyl-5α-androstan-3-one above results in the preparation of 3β,17β,19-tri(triphenylsiloxy)-5α-androstane, 19-hydroxy-3β-triphenylsiloxy-5α-androstan-17-one acetate and 3-hydroxy-19-triphenylsiloxy-5α-androstan-17-one acetate, respectively.

Sources & evidence

ORD record
ord-3886fbb338da43f5852c6d1f70cbb143
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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