Baccatin Iii → HCID 101380543, compound

HRID 1792886Notes

Reaction equation

HRID 1792886 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]([O:39][C:40]([CH3:42])=[O:41])[C:5]([C@@:7]1(C)[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(OC(C)=O)[CH2:31][O:32][C@@H:10]2[CH2:9][C@@H:8]1[OH:37])=[O:6]>CC(C)=O.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[C:19](=[O:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:16])([CH3:17])[C:3]=1[CH:4]([O:39][C:40]([CH3:42])=[O:41])[C:5]([C@@H:7]1[CH:8]([OH:37])[CH2:9][CH:10]3[C@@H:11]([CH2:31][O:32]3)[C@H:12]1[C@@H:13]2[O:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24])=[O:6]

Participants

4

Reactant 1

HCID 65366Baccatin Iii

Product 1

HCID 101380543HCID 101380543, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

Baccatin III (150 g, 0.25 mol) was dissolved in acetone (1.43 L). Commercially available manganese dioxide (450 g) was added in three portions under strong stirring. After the starting product disappeared (4 h) the suspension was filtered and the solvent evaporated off. The crude was suspended in AcOEt (100 ml) and refluxed for 1 h, then c-Hexane (100 ml) was added. The title compound was obtained from mother liquors, after evaporation of the solvent, as a white solid (140 g, 95%).

Workup

  1. custom(4 h)
  2. filtrationwas filtered
  3. customthe solvent evaporated off
  4. temperaturerefluxed for 1 h
  5. additionc-Hexane (100 ml) was added

Sources & evidence

ORD record
ord-c16a04ff9cf74e0790281c4fe09f889b
Source dataset
uspto-grants-2006_07
Patent number
US07078432B2

Reaction notes

Loading…