Paclitaxel → 10-Deacetyltaxol

HRID 377956Notes

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:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[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].I([O-])(=O)(=O)=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:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[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: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

Reactant 2

HCID 36314Paclitaxel

HCID 167232Periodate

Product 1

HCID 15583110-Deacetyltaxol

Procedure

where R represents C6H5 (taxol analogue A or xyloside A), or CH3C=CHCH3 (taxol analogue B or xyloside B) or C5H11 (taxol analogue C or xyloside C) in a polar solvent (b) reacting the resultant solution with periodate for 20-40 hours at 20-40° C. to cleave the diol system of the xyloside into dialdehyde, (c) treating the generated dialdehyde in a mixture of polar solvent-organic acid mixture with salts of amines at 0-40° C. for 12-18 hours and (d) isolating the 10-deacetyl taxol A,B,C by chromatography.

Workup

customfor 20-40 hours
customat 20-40° C.

Sources & evidence

ORD record: ord-80f7ccf85464498ab0d76d99717e6c57
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06028206

Reaction notes

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