HCID 22806915, compound → HCID 22806916, compound

HRID 1390758Notes

Reaction equation

[C:1](OC[C@@]12[C@@H]3[C@H]([C@H]4[C@@](CC3)(C)[C@@H](O)CC4)CC=C1C[C@@H](O)CC2)(=[O:3])[CH3:2].[CH3:26][Si:27]([CH3:59])([CH3:58])[O:28][C@H:29]1[CH2:46][CH2:45][C@@:44]2([CH2:47][O:48][Si](C)(C)C)[C:31](=[CH:32][CH2:33][C@@H:34]3[C@@H:43]2[CH2:42][CH2:41][C@@:39]2([CH3:40])[C@H:35]3[CH2:36][CH2:37][C@@H:38]2[O:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[CH2:30]1>>[C:1]([O:48][CH2:47][C@@:44]12[C@@H:43]3[C@H:34]([C@H:35]4[C@@:39]([CH2:41][CH2:42]3)([CH3:40])[C@@H:38]([O:53][Si:54]([CH3:56])([CH3:57])[CH3:55])[CH2:37][CH2:36]4)[CH2:33][CH:32]=[C:31]1[CH2:30][C@@H:29]([O:28][Si:27]([CH3:59])([CH3:26])[CH3:58])[CH2:46][CH2:45]2)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 22806915HCID 22806915, compound

HCID 70605278HCID 70605278, compound

Product 1

HCID 22806916HCID 22806916, compound

Procedure

Following essentially the same procedure but substituting 17α-methyl-5-androstene-3β,17β,19-triol 3,17-diacetate, androst-5-ene-3β,17β,19-triol 19-acetate, and 4α-methyl-17β,19-di(2'-tetrahydropyranyloxy)-5-androsten-3β-ol for the androst-5-ene-3β,17β,19-triol above results in the formation of 17α-methyl-3β,17β,19-tri(trimethylsiloxy)androst-5-ene, 3β,17β-di(trimethylsiloxy)-5-androsten-19-ol acetate and 4α-methyl-17β,19-di(2'-tetrahydropyranyloxy)-3β-trimethylsiloxy-5-androstene, respectively.

Sources & evidence

ORD record: ord-a9ab014920a645a6948359686a28b602
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04139617

Reaction notes

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