Chlorotrimethylsilane → Dihydroartemisinin ethyl ether

HRID 353352노트

반응식

HRID 353352 반응식
[CH3:1][C@H:2]1[C@@H:12]2[CH2:13][CH2:14][C@:15]3([CH3:19])[O:17][O:18][C@:11]42[C@H:5]([C@@H:6]([CH3:20])[C:7]([O:9][C@@H:10]4[O:16]3)=[O:8])[CH2:4][CH2:3]1.O=[CH:22][C@@H:23]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[BH4-].[Na+].Cl[Si](C)(C)C>C(O)C>[CH3:22][CH2:23][O:8][C@H:7]1[O:9][C@@H:10]2[O:16][C:15]3([CH3:19])[O:17][O:18][C@@:11]42[C@@H:5]([CH2:4][CH2:3][C@@H:2]([CH3:1])[C@@H:12]4[CH2:13][CH2:14]3)[C@H:6]1[CH3:20]

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 4311764Sodium borohydrideHCID 9838675Qing Hau Sau

생성물 1

HCID 72416Dihydroartemisinin ethyl ether수율 72.8%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
21.5 °C

실험 절차

Artemisinin (1 g.) and polyhydroxy catalyst, dextrose (4 g.) were stirred in ethanol (15 ml). Sodium borohydride (500 mg.) was added slowly for 10 minutes and the reaction mixture was stirred for 30 minutes at room temperature (20-23° C.). After completion of the reduction step, chlorotrimethysilane (3.5 ml) was added and the reaction mixture was further stirred for 1.5 hours at room temperature. After usual work up and purification through column chromatography (1:5 ratio) a mixture of alpha and beta arteether (0.805 g., 80.5% w/w) were obtained.

후처리

  1. stirringthe reaction mixture was further stirred for 1.5 hours at room temperature
  2. customAfter usual work up and purification through column chromatography (1:5 ratio)
  3. additiona mixture of alpha

출처 및 근거

ORD 기록
ord-291903af93754e7dade38971f634d5e8
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750356B1

반응 노트

불러오는 중…