反应详情

To a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-(tert-butyldimethylsiloxy)-3"-hydroxycyclohexyl)-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 (300 mg) in 9 ml 33% methylene chloride in cyclohexane was added allyl trichloroacetimidate (138 mg neat) and the reaction mixture was allowed to mix for 5 minutes. Trifluoromethanesulfonic acid (18 μl neat) was added slowly via syringe and the mixture stirred at room temperature. After 3 days the reaction was diluted with ethyl acetate and quenched with saturated sodium bicarbonate. The layers were separated, and the organic layer was washed with brine then dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate: hexane (1:4)+1% methanol) gave the title compound (230 mg; trichloroacatamide present). 1H NMR consistent with the desired structure.

1. additionto mix for 5 minutes
2. customquenched with saturated sodium bicarbonate
3. customThe layers were separated
4. washthe organic layer was washed with brine
5. dry with materialthen dried over magnesium sulfate
6. customPurification of the
7. concentrationconcentrate by flash chromatography on silica gel (ethyl acetate: hexane (1:4)+1% methanol)