Chlorotrimethylsilane → Dihydroartemisinin ethyl ether

HRID 353352

Reaktionsgleichung

Reaktionsgleichung von HRID 353352
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 72416Dihydroartemisinin ethyl etherAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
21.5 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-291903af93754e7dade38971f634d5e8
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750356B1

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