Tributylstannane → tert-butyldiphenyl(((5S,6aR)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)silane

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Reaction Steps

A solution of tert-butyl(((5R,6S,6aS)-6-iodo-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)diphenylsilane (from step 6) (10.3 g, 0.0186 mol), Bu3SnH (5.9 mL, 0.0224 mol) and AIBN (5 mol %) in 120 mL anhydrous toluene was refluxed for 7 h. The reaction mixture was cooled to room temperature and 100 mL of 1N NaOH was added and stirred for one h. This mixture was then finally washed with brine and extracted with ethyl acetate. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Purification was performed by column chromatography using hexane and ethyl ether as a gradient mixture to give 6.8 g of viscous title compound in 86% yield.

Provenance & Evidence