Tigogenin → 3-Hydroxypregna-5,16-dien-20-one

HRID 1275378Notes

Reaction equation

HRID 1275378 reaction equation
C[C@H]1CO[C@@]2(O[C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH2:18][C@H:19]6[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H]2C)CC1.C[C:32]1[C@@H]2[C@]3(C)[C@@H](C[C@@H]2[O:34][C:33]=1CC[C@H](CO)C)[C@@H]1CC=C2C[C@@H](O)CC[C@]2(C)[C@H]1CC3>C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[OH:25][CH:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[C:19](=[CH:18][CH2:17][C@@H:16]3[C@@H:15]2[CH2:14][CH2:13][C@@:12]2([CH3:27])[C@H:11]3[CH2:10][CH:8]=[C:7]2[C:33](=[O:34])[CH3:32])[CH2:24]1

Participants

5

Reactant 2

HCID 99516TigogeninHCID 10573853HCID 10573853, compound2×

Product 1

HCID 128405703-Hydroxypregna-5,16-dien-20-one

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Procedure

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.

Sources & evidence

ORD record
ord-4556161d58e24a088bfd440d4cb5ca42
Source dataset
uspto-grants-2000_12
Patent number
US06160139

Reaction notes

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