7-Xylosyl-10-deacetyltaxol C → 10-Deacetyltaxol C

HRID 377957Notes

Reaction equation

HRID 377957 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C@H:9]([C@@H:16]([OH:67])[C:17]([O:19][C@@H:20]1[C:50]([CH3:51])=[C:49]2[C:52]([CH3:54])([CH3:53])[C@:22]([OH:66])([C@@H:23]([O:57][C:58]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[O:59])[C@@H:24]3[C@:29]4([O:32][C:33]([CH3:35])=[O:34])[CH2:30][O:31][C@@H:28]4[CH2:27][C@H:26]([O:36][C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@@:25]3([CH3:56])[C:46]([C@@H:48]2[OH:55])=[O:47])[CH2:21]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].I([O-])(=O)(=O)=O.[Na+]>C(O)C.O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C@H:9]([C@@H:16]([OH:67])[C:17]([O:19][C@@H:20]1[C:50]([CH3:51])=[C:49]2[C:52]([CH3:54])([CH3:53])[C@:22]([OH:66])([C@@H:23]([O:57][C:58]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[O:59])[C@@H:24]3[C@:29]4([O:32][C:33]([CH3:35])=[O:34])[CH2:30][O:31][C@@H:28]4[CH2:27][C@H:26]([OH:36])[C@@:25]3([CH3:56])[C:46]([C@@H:48]2[OH:55])=[O:47])[CH2:21]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

5

Reactant 2

HCID 152223147-Xylosyl-10-deacetyltaxol CHCID 23667635Sodium periodate

Product 1

HCID 987571610-Deacetyltaxol C

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

To a small reaction flask was added the analogue 7-xylosyl-10-deacetyl taxol C (200 mg) in ethanol (300 ml); Sodium periodate (450 mg in 4 ml water) was added to the resulting solution and the reaction mixture was stirred for 20-40 hours at 20-40° C. The reaction mixture was diluted with water and extracted with ethyl acetate (2×50 ml). The ethyl acetate phase was washed with water, dried over anhydrous sodium sulphate and concentrated in vacuo to a residue. The residue was dissolved in a mixture of methanol--acetic acid and was treated with diethyl hydrozine sulphate (500 mg) for 12-18 hours at 0-40° C. with stirring. The reaction mixture was diluted with water and extracted with chloroform (2×50 ml). The chloroform layer was washed with water (2×50 ml), dried over anhydrous sodium sulphate and concentrated in vacuo to give a residue of 10-DAT, C.

Workup

  1. extractionextracted with ethyl acetate (2×50 ml)
  2. washThe ethyl acetate phase was washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo to a residue
  5. dissolutionThe residue was dissolved in a mixture of methanol
  6. additionacetic acid and was treated with diethyl hydrozine sulphate (500 mg) for 12-18 hours at 0-40° C.
  7. stirringwith stirring
  8. additionThe reaction mixture was diluted with water
  9. extractionextracted with chloroform (2×50 ml)
  10. washThe chloroform layer was washed with water (2×50 ml)
  11. dry with materialdried over anhydrous sodium sulphate
  12. concentrationconcentrated in vacuo
  13. customto give a residue of 10-DAT, C

Sources & evidence

ORD record
ord-70f703a890654d2dba9fe7246942bbc5
Source dataset
uspto-grants-2000_02
Patent number
US06028206

Reaction notes

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