Paclitaxel → 10-deacetylbaccatin III

HRID 1657326Notes

Reaction equation

HRID 1657326 reaction equation
[CH3:1][C:2]1[C@@H:19]([O:20]C([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)[CH2:18][C@:14]2([OH:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:59]C(C)=O)[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6].[BH4-].[Na+]>[Co](Cl)Cl.COCCOC>[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([OH:59])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6]

Participants

5

Reactant 2

HCID 36314PaclitaxelHCID 4311764Sodium borohydride

Product 1

HCID 15427210-deacetylbaccatin IIIYield 21%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In the third embodiment, 7% cobalt chloride (based on the taxol in the starting material) was added to the reaction solvent, CH3OCH2CH2OCH3 (glyme) and contacted with sodium borohydride at room temperature for 144 hours. This process resulted in a 21% yield of 10-deacetylbaccatin III. A low positive yield of 10-deacetylbaccatin III was also obtained in a similar experiment using 0.1% SnCl2.

Sources & evidence

ORD record
ord-9d70cfda33f94022a212a79736e316d3
Source dataset
uspto-grants-1993_10
Patent number
US05256801

Reaction notes

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