Chlorotrimethylsilane → Dihydroartemisinin ethyl ether

HRID 353352

Reaction equation

HRID 353352 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 72416Dihydroartemisinin ethyl etherYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
21.5 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-291903af93754e7dade38971f634d5e8
Source dataset
uspto-grants-2004_06
Patent number
US06750356B1

Linked notes

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