Phosphate → HCID 66937743, compound

Participants

Reaction Steps

(2S,3aS,4E,6S,7S,13aR)-11-{[tert-butyl(dimethyl)silyl]oxy}-7-{(1E)-3-[(4-methoxybenzyl)oxy]-1-methylprop-1-en-1-yl}-6,13a-dimethyl-2-phenyl-3a,6,7,10,11,12,13,13a-octahydro-9H-[1,3]dioxolo[4,5-f]oxacyclododecin-9-one (710 mg, 1.09 mmol) was dissolved in dichloromethane (14.0 ml) and a phosphate buffer (pH=7, 1.40 ml). 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (297 mg, 1.31 mmol) was added to the reaction solution at 0° C. and stirred for three hours. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (74.3 mg, 0.33 mmol) was added and the reaction solution was stirred at 0° C. for one and a half hour. After 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (74.3 mg, 0.33 mmol) was added and the reaction solution was stirred at 0° C. for further 30 minutes, the reaction solution was filtered with silica gel (Fuji Silysia, commercial name Chromatorex, NH, 200-350 mesh). The filtrate was washed with a saturated sodium hydrogen carbonate aqueous solution, distilled water and brine sequentially and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=4:1→3:1) to obtain the title compound (460 mg) as a colorless needle.

Provenance & Evidence