Taccalonolide A → Taccalonolide B

HRID 525290ノート

反応式

HRID 525290 の反応式
[CH3:1][C@H:2]1[C@@H:7]2[C@@:8]3([CH3:43])[C@@H:18]([O:19][C:20]([CH3:22])=[O:21])[C@@H:17]([O:23][C:24]([CH3:26])=[O:25])[C@@H:16]4[C@@:27]5([CH3:42])[C@@H:32]([O:33][C:34]([CH3:36])=[O:35])[C@H:31]6[O:37][C@H:30]6[CH2:29][C@@H:28]5[C:38]([C@H:40]([OH:41])[C@H:15]4[C@@H:9]3[C@@H:10]([O:11]C(C)=O)[C@H:6]2[C@@:5]2([CH3:50])[C@@:44]([OH:49])([CH3:48])[C:45]([O:47][C:4]2=[CH:3]1)=[O:46])=[O:39]>CO.C(=O)(O)[O-].[Na+]>[CH3:1][C@H:2]1[C@@H:7]2[C@@:8]3([CH3:43])[C@@H:18]([O:19][C:20]([CH3:22])=[O:21])[C@@H:17]([O:23][C:24]([CH3:26])=[O:25])[C@@H:16]4[C@@:27]5([CH3:42])[C@@H:32]([O:33][C:34]([CH3:36])=[O:35])[C@H:31]6[O:37][C@H:30]6[CH2:29][C@@H:28]5[C:38]([C@H:40]([OH:41])[C@H:15]4[C@@H:9]3[C@@H:10]([OH:11])[C@H:6]2[C@@:5]2([CH3:50])[C@@:44]([OH:49])([CH3:48])[C:45]([O:47][C:4]2=[CH:3]1)=[O:46])=[O:39]

参加物

4

反応物 1

HCID 441685Taccalonolide A

生成物 1

HCID 56662029Taccalonolide B収率 68.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Taccalonolide A (40 mg) was dissolved in 4 mL of methanol and to this solution 8 mL of 0.05 M sodium bicarbonate was added. The solution was stirred at room temperature for 44 hours. The reaction solution was extracted with EtOAc and purified on HPLC to yield 25.8 mg of taccalonolide B. Taccalonolides N and AB were produced by hydrolysis of taccalonolides E and Z, respectively, using the same method. Taccalonolide AB was obtained as white powder. The LC/MS showed pseudomolecular ions at 677 [M+H]+, 694 [M+NH4]+, and 699 [M+Na]+, indicating the loss of an acetyl group from taccalonolide Z. The proton NMR showed the chemical shift of H-15 of taccalonolide AB at δ 4.75 (ddd, J=3.5, 9.0, 11.6 Hz), which is shifted 0.78 ppm up-field than that of taccalonolide Z, suggesting the loss of acetyl group at 15-OH. The HMBC correlation between 15-OH (δ 4.94) and C-15 (δ 71.5) confirmed the assignment.

後処理

  1. additionwas added
  2. extractionThe reaction solution was extracted with EtOAc
  3. custompurified on HPLC

出典と根拠

ORDレコード
ord-26432529736c47cda4ac870cf6c3c579
出典データセット
uspto-grants-2016_05
特許番号
US09340572B2

反応ノート

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