Periodate → 10-deacetylbaccatin III

HRID 2304883Notes

Reaction equation

HRID 2304883 reaction equation
[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([OH:48])[C:5]([C@@:7]1([CH3:47])[C@H:12]([C@@H:13]2[O:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9][C@@H:8]1[O:37][C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O)=[O:6].I([O-])(=O)(=O)=O>>[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([OH:48])[C:5]([C@@:7]1([CH3:47])[C@H:12]([C@@H:13]2[O:22][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9][C@@H:8]1[OH:37])=[O:6]

Participants

3

Reactant 2

HCID 167232PeriodateHCID 53153567-Xylosyl-10-deacetylbaccatin III

Product 1

HCID 15427210-deacetylbaccatin III

Procedure

by dissolving the taxol analogue of formula 2 in a polar solvent, reacting the resultant solution with a base at a temperature of 20-50° C. for a time period in the range of 20-40 hours, and isolating 7-xyloxyl-10-deacetylbaccatin III, dissolving the 7-xylosyl-10-deacetylbaccatin III in a polar solvent, reacting the resultant solution with a periodate at 20-40° C. for a time period in the range of 20-40 hours to cleave the diol system of the xyloside into dialdehyde, treating the generated dialdehyde in an organic acid medium with salts of amine at 0-40° C. for 12-18 hours and isolating 10-deacetylbaccatin III of formula 1.

Workup

  1. customat 20-40° C.
  2. customin the range of 20-40 hours

Sources & evidence

ORD record
ord-45a0f9964639447f856f850b040aa901
Source dataset
uspto-grants-2002_08
Patent number
US06437154B1

Reaction notes

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