Taccalonolide A → Taccalonolide B

HRID 525290노트

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HRID 525290 반응식
[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]

참가 물질

4

반응물 1

HCID 441685Taccalonolide A

생성물 1

HCID 56662029Taccalonolide B수율 68.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-26432529736c47cda4ac870cf6c3c579
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340572B2

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