4-Toluenesulfonyl chloride → (2S)-2-Methoxy-2-{2-[(4-methylbenzene-1-sulfonyl)oxy]ethoxy}ethyl 4-methylbenzene-1-sulfonate

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Reaction Steps

1,5-dihydroxy-2(S)-methoxy-3-oxa-pentane (E4) (1.4 g, 10.3 mmole), prepared as described in Example 8, was dissolved in dry pyridine (10 ml) and treated at 0° C. with p-toluensulfonylchloride (6.4 g, 0.034 mole). The mixture was kept at 4° C. overnight, then was poured into an ice-water mixture and finally extracted with methylene chloride. The organic phase was washed with water, separated off, dried over anhydrous sodium sulphate, filtered off. The solvent was removed under reduced pressure. The crude material was chromatographed on a silicic acid column using methylene chloride as eluting agent to give 2.8 g (yield 62%) of pure title derivative,

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