2-Dimethylaminopyridine → {6-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-2,3,4,5-tetrahydroxy-hexyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

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Reaction Steps

Compound 35 (5.0 g, 12.4 mmol) was dissolved in 100 ml of pyridine and azeotropically boiled. After this operation was conducted two times, the product was dissolved in 100 ml of dry pyridine and cooled with ice in a nitrogen stream. 4,4′-Dimethoxytrityl chloride (5.0 g, 14.9 mmol) and dimethylaminopyridine (1.5 g, 12.4 mmol) were added, the temperature was gradually increased from under ice cooling to room temperature, and this was followed by stirring at room temperature for 17 hours. After the pyridine was evaporated under reduced pressure, the residue was diluted with 500 ml of ethyl acetate. After water was added, the organic phase was separated, after which the water phase was again extracted with ethyl acetate. The ethyl acetate phase was washed with saturated brine, after which it was dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the concentrate was purified by silica gel column chromatography (CHCl3:MeOH=10:1) to yield the desired compound (Compound 36: 5.06 g) at a percent yield of 57.9%.

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