Reaktion #1477950

ord-7cd645e76005409d8f763e6cfa22a618

Reaktionsgleichung

CC(C)(C)[Si](C)(C)OC[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-hydroxy-4-androstene-3,17-dione
CC(C)(C)[Si](C)(C)OC[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-t-butyldimethylsiloxy-4-androstene-3,17-dione
C[C@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(CO)CCC(=O)C=C12
19-hydroxy-6α-methyl-4-androstene-3,17-dione
→
CC(=O)O.CC(C)(C)[Si](C)(C)OC1CC[C@@]2(CO)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1
3-t-butyldimethylsiloxy-19-hydroxy-5-androsten-17-one acetate
C[C@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(CO[Si](C)(C)C(C)(C)C)CCC(=O)C=C12
19-t-butyldimethylsiloxy-6α-methyl-4-androstene-3,17-dione

Edukte

CC(C)(C)[Si](C)(C)OC[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-hydroxy-4-androstene-3,17-dione
CC(C)(C)[Si](C)(C)OC[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-t-butyldimethylsiloxy-4-androstene-3,17-dione
C[C@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(CO)CCC(=O)C=C12
19-hydroxy-6α-methyl-4-androstene-3,17-dione
—
3β,19-dihydroxy-5-androsten-17-one 19-acetate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Following essentially the same procedure and substituting 19-hydroxy-6α-methyl-4-androstene-3,17-dione and 3β,19-dihydroxy-5-androsten-17-one 19-acetate for the 19-hydroxy-4-androstene-3,17-dione above results in the preparation of 19-t-butyldimethylsiloxy-6α-methyl-4-androstene-3,17-dione and 3-t-butyldimethylsiloxy-19-hydroxy-5-androsten-17-one acetate, respectively.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04139617uspto-grants-1979_02