Reacción #6395

Ecuación de reacción

17-ethyl-1,14-dihydroxy-12-[2'-(3",4"-dihydroxycyclohexyl)-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

isopropyl trichloroacetimidate

Trifluoromethanesulfonic acid

→

title compounds

17-Ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-isopropoxycyclohexyl)-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

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONto mix for 5 minutes
2. 2
   OtroAfter 3 hours the reaction was quenched by the addition of saturated sodium bicarbonate
3. 3
   Extracciónextracted with ethyl acetate (3×5 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 preparative TLC on silica gel (ethyl acetate:hexane (1:1)+1% methanol)

Procedimiento

To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(3",4"-dihydroxycyclohexyl)-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 (110 mg in 1.5 ml 33% methylene chloride in cyclohexane), isopropyl trichloroacetimidate (52 μl neat) was added and the reagents allowed to mix for 5 minutes. Trifluoromethanesulfonic acid (2 μl neat) was added slowly via syringe and the mixture stirred at room temperature. After 3 hours the reaction was quenched by the addition of saturated sodium bicarbonate and extracted with ethyl acetate (3×5 ml). The combined organics were washed with brine and dried over magnesium sulfate. Purification of the concentrate by preparative TLC on silica gel (ethyl acetate:hexane (1:1)+1% methanol) gave the title compounds (15 mg 4"-ether; 16 mg 3"-ether).

Fuente