Reaktion #1477926

ord-3e426947b3ad4336905770d6812e941a

Reaktionsgleichung

CC1=C2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O)CC[C@@H]34)[C@@]2(CO)CCC1=O
17β,19-dihydroxy-4-methyl-4-androsten-3-one
CC1=C2C[C@@H](C)[C@@H]3[C@H](CC[C@]4(C)[C@@H](O)CC[C@@H]34)[C@@]2(CO)CCC1=O
17β,19-dihydroxy-4,7α-dimethyl-4-androsten-3-one
CC1=C2CC[C@@H]3[C@H](CC[C@]4(C)C(=O)CC[C@@H]34)[C@@]2(CO)[C@@H](C)CC1=O
19-hydroxy-1α,4-dimethyl-4-androstene-3,17-dione
→
C[C@@H]1C(=O)CC[C@@]2(CO)C1=CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
17β,19-dihydroxy-4α-methyl-5-androsten-3-one
C[C@@H]1C(=O)C[C@H](C)[C@@]2(CO)C1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-hydroxy-1α,4α-dimethyl-5-androstene-3,17-dione
C[C@@H]1C(=O)CC[C@@]2(CO)C1=C[C@@H](C)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
17β,19-dihydroxy-4α,7α-dimethyl-5-androsten-3-one

Edukte

CC1=C2CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O)CC[C@@H]34)[C@@]2(CO)CCC1=O
17β,19-dihydroxy-4-methyl-4-androsten-3-one
CC1=C2C[C@@H](C)[C@@H]3[C@H](CC[C@]4(C)[C@@H](O)CC[C@@H]34)[C@@]2(CO)CCC1=O
17β,19-dihydroxy-4,7α-dimethyl-4-androsten-3-one
—
4-methyl-17β,19-di(2'-tetrahydropyranyloxy)-4-androsten-3-one
—
17β,19-dihydroxy-4,6α,17α-trimethyl-4-androsten-3-one
—
1α,4-dimethyl-19-(2'-tetrahydropyranyloxy)-4-androstene-3,17-dione
CC1=C2CC[C@@H]3[C@H](CC[C@]4(C)C(=O)CC[C@@H]34)[C@@]2(CO)[C@@H](C)CC1=O
19-hydroxy-1α,4-dimethyl-4-androstene-3,17-dione

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Substituting 17β,19-dihydroxy-4-methyl-4-androsten-3-one, 19-hydroxy-1α,4-dimethyl-4-androstene-3,17-dione, 17β,19-dihydroxy-4,7α-dimethyl-4-androsten-3-one, 4-methyl-17β,19-di(2'-tetrahydropyranyloxy)-4-androsten-3-one and 1α,4-dimethyl-19-(2'-tetrahydropyranyloxy)-4-androstene-3,17-dione for the 17β,19-dihydroxy-4,6α,17α-trimethyl-4-androsten-3-one above results in the formation of 17β,19-dihydroxy-4α-methyl-5-androsten-3-one, 19-hydroxy-1α,4α-dimethyl-5-androstene-3,17-dione, 17β,19-dihydroxy-4α,7α-dimethyl-5-androsten-3-one, 4α-methyl-17β,19-di(2'-tetrahydropyranyloxy)-5-androsten-3-one and 1α,4α-dimethyl-19-(2'-tetrahydropyranyloxy)-5-androstene-3,17-dione, respectively.

Quelle

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