Chlorotrimethylsilane → Dihydroartemisinin ethyl ether

HRID 353352

反応式

HRID 353352 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 72416Dihydroartemisinin ethyl ether収率 72.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
21.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-291903af93754e7dade38971f634d5e8
出典データセット
uspto-grants-2004_06
特許番号
US06750356B1

関連ノート

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