Reaktion #1362560

ord-4556161d58e24a088bfd440d4cb5ca42

Reaktionsgleichung

C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C
tigogenin
CC1=C(CC[C@@H](C)CO)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@H]12
pseudodiosgenin
CC1=C(CC[C@@H](C)CO)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@H]12
pseudodiosgenin
→
CC(=O)C1=CC[C@H]2[C@@H]3CC=C4CC(O)CC[C@]4(C)[C@H]3CC[C@]12C
3-hydroxy-5-pregnen-16-en-20-one

Edukte

C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C
tigogenin
CC1=C(CC[C@@H](C)CO)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@H]12
pseudodiosgenin
CC1=C(CC[C@@H](C)CO)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@H]12
pseudodiosgenin

Reagenzien

[Cr+6].[O-2].[O-2].[O-2]
chromium trioxide

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

In this method too tigogenin is converted by conventional method to pseudodiosgenin and finally pseudodiosgenin is oxidized with chromium trioxide in acetic acid to give 3-hydroxy-5-pregnen-16-en-20-one.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06160139uspto-grants-2000_12