Reaktion #459037

ord-a8fb380a8c064170953ec4546e3abef0

Reaktionsgleichung

C[C@@H]1CC2=C[C@@H](O)CC[C@]2(CO)[C@H]2CC[C@]3(C)[C@@H](O)CC[C@H]3[C@H]12
7α-methyl-4-androstene-3β,17β,19-triol
CC1=C2C[C@@H](C)[C@@H]3[C@H](CC[C@]4(C)[C@@H](O)CC[C@@H]34)[C@@]2(CO)CC[C@@H]1O
4,7α-dimethyl-4-androstene-3β,17β,19-triol
→
CC#C[C@]1(O)CC[C@H]2[C@@H]3[C@H](C)CC4=CC(=O)CC[C@]4(CO)[C@H]3CC[C@@]21C
17β,19-dihydroxy-7α-methyl-17α-propinyl-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

Edukte

—
7α,17α-dimethyl-4-androstene-3β,17β,19-triol
C[C@@H]1CC2=C[C@@H](O)CC[C@]2(CO)[C@H]2CC[C@]3(C)[C@@H](O)CC[C@H]3[C@H]12
7α-methyl-4-androstene-3β,17β,19-triol
—
7α-methyl-17α-propinyl-4-androstene-3β,17β,19-triol
CC1=C2C[C@@H](C)[C@@H]3[C@H](CC[C@]4(C)[C@@H](O)CC[C@@H]34)[C@@]2(CO)CC[C@@H]1O
4,7α-dimethyl-4-androstene-3β,17β,19-triol

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Substituting 4,7α-dimethyl-4-androstene-3β,17β,19-triol, 7α,17α-dimethyl-4-androstene-3β,17β,19-triol and 7α-methyl-17α-propinyl-4-androstene-3β,17β,19-triol for the 7α-methyl-4-androstene-3β,17β,19-triol above results in the formation of 17β,19-dihydroxy-4,7α-dimethyl-4-androsten-3-one, 17β,19-dihydroxy-7α,17α-dimethyl-4-androsten-3-one and 17β,19-dihydroxy-7α-methyl-17α-propinyl-4-androsten-3-one, respectively.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04087524uspto-grants-1978_05