反应详情

A solution of tert-butyl (3S,6R,7S,8S,10E,12Z,15S,16E)-5-oxo-3,15-bis(triethylsilyloxy)-17-(2-(2,2,2-trichloroethoxycarbonyloxymethyl)thiazol-4-yl)-4,4,6,8,12,16-hexamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-heptadeca-10,12,16-trienoate (2.8 g) in 12 mL of CH2Cl2 is treated with 2,6-lutidine (0.86 mL) and triethylsilyl trifluoromethanesulfonate (0.98 g) at 0° C. for 30 minutes, then at ambient temperature for 10 hours. The mixture is diluted with 50 mL of ethyl acetate and poured into 20 mL of 1 N HCl. The organic phase is separated, washed with pH 7 phosphate buffer, dried with Na2SO4, filtered, and concentrated. The residue is dissolved in 5 mL of THF and treated with 0.5 mL of 0.1 N HCl in methanol. The reaction is monitored by thin-layer chromatography, with additional aliquots of methanolic HCl being added to achieve complete reaction. When complete, the reaction is poured into 15 mL of pH 7 phosphate buffer and extracted with ethyl acetate. The extract is washed with brine, dried with Na2SO4, filtered, and evaporated. The product is purified by flash chromatography on SiO2 (1:1 hexanes/ethyl acetate).

1. customThe organic phase is separated
2. washwashed with pH 7 phosphate buffer
3. dry with materialdried with Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe residue is dissolved in 5 mL of THF
7. additiontreated with 0.5 mL of 0.1 N HCl in methanol
8. additionadded
9. customreaction
10. extractionextracted with ethyl acetate
11. washThe extract is washed with brine
12. dry with materialdried with Na2SO4
13. filtrationfiltered
14. customevaporated
15. customThe product is purified by flash chromatography on SiO2 (1:1 hexanes/ethyl acetate)