Tin tetrachloride → Baccatin Iii

HRID 1590326Notes

Reaction equation

HRID 1590326 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH3:6][C:7]1[C@@H:24]([O:25]C([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)[CH2:23][C@:19]2([OH:46])[C:20]([CH3:22])([CH3:21])[C:8]=1[C@@H:9]([O:64][C:65]([CH3:67])=[O:66])[C:10]([C@@:12]1([CH3:63])[C@H:17]([C@@H:18]2[O:47][C:48]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)=[O:49])[C@:16]2([O:58][C:59]([CH3:61])=[O:60])[CH2:56][O:57][C@@H:15]2[CH2:14][C@@H:13]1[OH:62])=[O:11].[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[CH3:6][C:7]1[C@@H:24]([OH:25])[CH2:23][C@:19]2([OH:46])[C:20]([CH3:21])([CH3:22])[C:8]=1[C@@H:9]([O:64][C:65]([CH3:67])=[O:66])[C:10]([C@@:12]1([CH3:63])[C@H:17]([C@@H:18]2[O:47][C:48]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)=[O:49])[C@:16]2([O:58][C:59]([CH3:61])=[O:60])[CH2:56][O:57][C@@H:15]2[CH2:14][C@@H:13]1[OH:62])=[O:11]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 36314PaclitaxelHCID 169536Tetrabutylammonium borohydride

Product 1

HCID 65366Baccatin IiiYield 121.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the third embodiment, the addition of 10% tin chloride (based on the taxol in the starting material) to tetrabutylammonium borohydride in dichloromethane at 0° C. for one hour resulted in a 121.7% yield of Baccatin III. It would appear material other then just the cephalomannine and taxol in the starting material was cleaved to produce Baccatin III. It is hypothesized that certain taxol compounds may be bound to sugars and other biological material and that these may have been converted to Baccatin III in this process.

Workup

  1. customat 0° C.
  2. customfor one hour

Sources & evidence

ORD record
ord-503b721ff9ea468aa89e5b1b492fb2d0
Source dataset
uspto-grants-1993_04
Patent number
US05202448

Reaction notes

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