Baccatin Iii → 7-Epi-10-deacetylbaccatin III

HRID 1780216Notes

Reaction equation

HRID 1780216 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(C)=O)[C:5]([C@@:7]1([CH3:38])[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]>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:39])[C:5]([C@@:7]1([CH3:38])[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 1

HCID 65366Baccatin Iii

Product 1

HCID 98721177-Epi-10-deacetylbaccatin III

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

When Baccatin III was used as the starting material the reaction using water as the solvent also proceeds to the 10-DAB product; however, with a prolonged reaction time the yield is low and the 7-epi-10-DAB was formed in considerable amounts.

Sources & evidence

ORD record
ord-508eee3512684f5ab248001e16e0d60d
Source dataset
uspto-grants-1997_05
Patent number
US05629433

Reaction notes

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