17beta,19-Dihydroxy-5-androsten-3-one → 19-t-Butyldimethylsiloxy-5-androstene-3alpha,17-diol

HRID 1390772Notes

Reaction equation

HRID 1390772 reaction equation
[O:1]([CH2:9][C@@:10]12[C@@H:27]3[C@H:18]([C@H:19]4[C@@:23]([CH2:25][CH2:26]3)([CH3:24])[C:22](=[O:28])[CH2:21][CH2:20]4)[CH2:17][CH:16]=[C:15]1[CH2:14][C:13](=[O:29])[CH2:12][CH2:11]2)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].O[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(CO)C(CC(=O)CC1)=CC3>>[O:1]([CH2:9][C@@:10]12[C@@H:27]3[C@H:18]([C@H:19]4[C@@:23]([CH2:25][CH2:26]3)([CH3:24])[CH:22]([OH:28])[CH2:21][CH2:20]4)[CH2:17][CH:16]=[C:15]1[CH2:14][C@H:13]([OH:29])[CH2:12][CH2:11]2)[Si:2]([C:5]([CH3:8])([CH3:6])[CH3:7])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 1174873217beta,19-Dihydroxy-5-androsten-3-oneHCID 7060535419-t-Butyldimethylsiloxy-5-androstene-3,17-dione

Product 1

HCID 7060573519-t-Butyldimethylsiloxy-5-androstene-3alpha,17-diol

Procedure

Substituting 19-t-butyldimethylsiloxy-5-androstene-3,17-dione, 4α-methyl-17β,19-di(4'-tetrahydropyranyloxy)-5-androsten-3-one and 1β-methyl-19-(4'-tetrahydropyranyloxy)-5-androstene-3,17-dione for the 17β,19-dihydroxy-5-androsten-3-one above results in the preparation of 19-t-butyldimethylsiloxy-5-androstene-3α,17-diol, 4α-methyl-17β,19-di(4'-tetrahydropyranyloxy)-5-androsten-3α-ol and 1β-methyl-19-(4'-tetrahydropyranyloxy)-5-androstene-3α,17β-diol, respectively.

Sources & evidence

ORD record
ord-86950ed2e3264be7af1ea97fded63bfb
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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