Acetate → 3-t-Butyldimethylsiloxy-5-androsten-17beta,19-diol

HRID 1390787Notes

Reaction equation

C(O)(=O)C.[O:5]([CH:13]1[CH2:30][CH2:29][C@@:28]2([CH2:31][OH:32])[C:15](=[CH:16][CH2:17][C@@H:18]3[C@@H:27]2[CH2:26][CH2:25][C@@:23]2([CH3:24])[C@H:19]3[CH2:20][CH2:21][C:22]2=[O:33])[CH2:14]1)[Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C([O-])(=O)C>>[O:5]([CH:13]1[CH2:30][CH2:29][C@@:28]2([CH2:31][OH:32])[C:15](=[CH:16][CH2:17][C@@H:18]3[C@@H:27]2[CH2:26][CH2:25][C@@:23]2([CH3:24])[C@H:19]3[CH2:20][CH2:21][C@@H:22]2[OH:33])[CH2:14]1)[Si:6]([C:9]([CH3:12])([CH3:10])[CH3:11])([CH3:8])[CH3:7]

Participants

Reactant 2

HCID 175Acetate

HCID 1317114283-t-Butyldimethylsiloxy-19-hydroxy-5-androsten-17-one acetate

Product 1

HCID 706051733-t-Butyldimethylsiloxy-5-androsten-17beta,19-diol

Procedure

Substituting 3-t-butyldimethylsiloxy-19-hydroxy-5-androsten-17-one acetate and 19-hydroxy-3β-(4'-tetrahydropyranyloxy)-5-androsten-17-one acetate for the 19-hydroxy-3β-(2'-tetrahydropyranyloxy)-5-androsten-17-one, acetate above results in the preparation of 3-t-butyldimethylsiloxy-5-androsten-17β,19-diol and 3β-(4'-tetrahydropyranyloxy)-5-androstene-17β,19-diol, respectively.

Sources & evidence

ORD record: ord-c7168d164d3c4698b9958b6a86c79cd4
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04139617

Reaction notes

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