Hydrogen Peroxide → 4-(3-{3-(Tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester

Participants

Reaction Conditions

Reaction Steps

4-(3-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-oxo-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester of 2.6 g (3.67 mmol) was dissolved in THF (40 ml). The solution was cooled to −78° C., and then, L-selectride (1 M.THF solution, 7.35 mmol) was slowly added thereto dropwise. The mixture was stirred at the above temperature for 2 hours, and the reaction was stopped with hydrogen peroxide (30% aqueous solution, 16 mmol). The reaction solution was stirred at 0° C. for 30 minutes, and then, extracted with diethyl ether. The combined organic layer was washed with water and brine, and then, dried over magnesium sulfate, filtered off, and concentrated under reduced pressure. The concentrate was subjected to column chromatography on a silica gel (hexane:ethyl acetate=4:1) to obtain 4-(3-{3-(tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester (2.3 g, yield: 90%).

Provenance & Evidence