Baccatin Iii → HCID 101380543, compound

HRID 2250835Notes

Reaction equation

HRID 2250835 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 I). 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 EtOAc (100 ml) and refluxed for 1 h, then c-Hex (100 ml) was added. The title compound was obtained from mother liquors, after evaporation of the solvent, as 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-Hex (100 ml) was added

Sources & evidence

ORD record
ord-d2654dd5a0ff4544a520cbff4ad89e12
Source dataset
uspto-grants-2008_01
Patent number
US07317113B2

Reaction notes

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