Reacción #6399

Ecuación de reacción

17-ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone

cyclohexane allyl trichloroacetimidate

Trifluoromethanesulfonic acid

→

title compound

17-Ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-allyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONto mix for 5 minutes
2. 2
   OtroAfter 17 hours the reaction was quenched by the addition of saturated sodium bicarbonate
3. 3
   Extracciónextracted with ethyl acetate (3×15 ml)
4. 4
   LavadoThe combined organics were washed with brine
5. 5
   Secadodried over magnesium sulfate
6. 6
   OtroPurification of the
7. 7
   Concentraciónconcentrate by flash chromatography on silica gel (ether: hexane (2:3))

Procedimiento

To a solution of 17-ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (820 mg in 9 ml 33% methylene chloride in cyclohexane allyl trichloroacetimidate (366 μl neat) was added and the reagents allowed to mix for 5 minutes. Trifluoromethanesulfonic acid (16 μl neat) was added slowly via syringe and the mixture stirred at room temperature. After 17 hours the reaction was quenched by the addition of saturated sodium bicarbonate and extracted with ethyl acetate (3×15 ml). The combined organics were washed with brine and dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (ether: hexane (2:3)) gave the title compound (800 mg). (1H NMR was consistent with the desired structure).

Fuente