Hydrogen Peroxide → (3 R,4S,7S) 3,7-dibenzyloxy-4-vinyl-1,1-dimethoxydodeca-5-ene

Temperatur

0 °C

To a suspension of 997 mg (3.67 mM) of o-nitrophenylselenium cyanide in 12 ml of anhydrous tetrahydrofuran was dropwise added 886 mg (1.83 mM) of (3R,4S,7S) 3,7-dibenzyloxy-4-(2'-hydroxyethyl)-1,1-dimethoxydodeca-5-ene [7] described above. The mixture was stirred for several minutes and 0.91 ml (3.67 mM) of tri-n-butylphosphine was dropwise added to the mixture. The reaction solution was stirred for ten minutes then cooled to 0° C. and 35% hydrogen peroxide aqueous solution was dropwise added thereto at the same temperature while stirring. After stirring for 3 hours, the aqueous phase was extracted with a solvent mixture of diethyl ether:hexane=7:3. The extracts were combined and washed sequentially with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The precipitated crystals were taken from the residue by filtration to give 776 mg (1.67 mM) of (3R,4 S,7S) 3,7-dibenzyloxy-4-vinyl-1,1-dimethoxydodeca-5-ene [8]. Yield, 91%.

1. stirringThe reaction solution was stirred for ten minutes
2. stirringat the same temperature while stirring
3. stirringAfter stirring for 3 hours
4. extractionthe aqueous phase was extracted with a solvent mixture of diethyl ether
5. washwashed sequentially with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution
6. dry with materialAfter drying over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. filtrationThe precipitated crystals were taken from the residue by filtration

ORD-Eintrag

ord-46ee8919d4c747428a686f3d77dc5b22

Quelldatensatz

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05220074