Paclitaxel → 10-deacetylbaccatin III

HRID 1657327Notes

Reaction equation

HRID 1657327 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].CC1[C@@H](OC([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)C[C@]2(O)C(C)(C)C=1[C@@H](O)C([C@@]1(C)[C@H]([C@@H]2OC(C2C=CC=CC=2)=O)[C@]2(OC(C)=O)CO[C@@H]2C[C@@H]1O)=O>ClCCl>[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

4

Reactant 2

HCID 36314PaclitaxelHCID 15583110-Deacetyltaxol

Product 1

HCID 15427210-deacetylbaccatin III

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In contrast, the same procedure as described in Example II was run on 10 grams of starting material having the same taxol and 10-deacetyltaxol percentages. The reaction solvent used was dichloromethane (as was used in the Magris, et al. procedure). The 10-deacetylbaccatin III yield was only 24%, 90 mg (a lower yield resulted from larger amounts of material) as analyzed by TLC. there as 69 mg of 10-deacetyltaxol remaining; 47% of the 10-deacetyltaxol was converted. Based on TLC analysis, the reaction in dichloromethane was run for one hundred twenty hours versus seventy-two hours.

Sources & evidence

ORD record
ord-04d5a214a67749328a1ac17c287b3c0f
Source dataset
uspto-grants-1993_10
Patent number
US05256801

Reaction notes

Loading…