Cephalomannine → Baccatin Iii

HRID 439696

Reaction equation

HRID 439696 reaction equation
C/C=C(/C(N[C@H]([C@@H](O)C([O:18][C@@H:19]1[C:40]([CH3:41])=[C:39]2[C:42]([CH3:44])([CH3:43])[C@:21]([OH:59])([C@@H:22]([O:50][C:51]([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)=[O:52])[C@@H:23]3[C@:28]4([O:31][C:32]([CH3:34])=[O:33])[CH2:29][O:30][C@@H:27]4[CH2:26][C@H:25]([OH:35])[C@@:24]3([CH3:49])[C:36]([C@@H:38]2[O:45][C:46]([CH3:48])=[O:47])=[O:37])[CH2:20]1)=O)C1C=CC=CC=1)=O)\C>CO>[CH3:41][C:40]1[C@@H:19]([OH:18])[CH2:20][C@:21]2([OH:59])[C:42]([CH3:43])([CH3:44])[C:39]=1[C@@H:38]([O:45][C:46]([CH3:48])=[O:47])[C:36]([C@@:24]1([CH3:49])[C@H:23]([C@@H:22]2[O:50][C:51]([C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)=[O:52])[C@:28]2([O:31][C:32]([CH3:34])=[O:33])[CH2:29][O:30][C@@H:27]2[CH2:26][C@@H:25]1[OH:35])=[O:37]

Participants

3

Reactant 1

HCID 6436208Cephalomannine

Product 1

HCID 65366Baccatin Iii

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 mg cephalomannine in 20 μl methanol was incubated with 2 ml supernatant for 17 hours on an end-over-end shaker (Fisher Roto-Rack). The solution was extracted with methylene chloride, the extract was evaporated, resuspended in methanol and analyzed by HPLC (Method 2 described following). Cephalomannine concentration was decreased from 0.175 mg/ml to 0 and 0.110 mg/ml baccatin III was produced (89 mol % yield based on analyzed initial cephalomannine concentration).

Workup

  1. extractionThe solution was extracted with methylene chloride
  2. customthe extract was evaporated
  3. concentrationCephalomannine concentration

Sources & evidence

ORD record
ord-208b36c2f30e497b893823663d617d18
Source dataset
uspto-grants-1996_05
Patent number
US05516676

Linked notes

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