Phenylhydrazine → Paclitaxel

HRID 2380416Notes

Reaction equation

HRID 2380416 reaction equation
[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:40])[C@@H:24]([NH:31][C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:68][C:69]([CH3:71])=[O:70])[C:5]([C@@:7]1([CH3:67])[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[O:57][C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O)=[O:6].C1(NN)C=CC=CC=1>C(#N)C.O>[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:40])[C@@H:24]([NH:31][C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:33])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:68][C:69]([CH3:71])=[O:70])[C:5]([C@@:7]1([CH3:67])[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]

Participants

5

Reactant 2

HCID 7516PhenylhydrazineHCID 11094265Taxol-7-xyloside

Product 1

HCID 36314Paclitaxel

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In the manner of the procedure of Example 1, 0.5 g of taxol-7-xyloside was oxidatively cleaved. The product, after treatment with phenylhydrazine, was taken up in 25% acetonitrile in water and applied to a column of 10 g of C-18 reverse phase silica. The column was eluted with a gradient of acetonitrile in water (30, 35, 40, 45, and 50%).

Workup

  1. washThe column was eluted with a gradient of acetonitrile in water (30, 35, 40, 45, and 50%)

Sources & evidence

ORD record
ord-9111c24790c2490f8ebe0374d3ab90f4
Source dataset
uspto-grants-1994_11
Patent number
US05367086

Reaction notes

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