Potassium Carbonate → (3'r,4's,5s,5's,6'r)-3',4',5'-Tris-benzyloxy-6'-benzyloxymethyl-3-[(4-ethylphenyl)methyl]-3',4',5',6'-tetrahydro-spiro[thieno[2,3,f]isobenzofuran-5(7h),2'-[2h]pyran]

Participants

Reaction Conditions

Reaction Steps

(3′R,4′S,5S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-3-iodo-3′,4′,5′,6′-tetrahydro-spiro[thieno[2,3,f]isobenzofuran-5(7H),2′-[2H]pyran] (0.05 g, 0.061 mmol), potassium carbonate (25.5 mg, 0.184 mmol), silver oxide (35.6 mg, 0.154 mmol) and diphenylphosphino ferrocene palladium dichloride (5.1 mg, 0.006 mmol) were dissolved in 1,4-dioxane (0.308 mL). To the resultant solution was added 2-(4-ethyl-benzyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborane (18.2 mg, 0.073 mmol), and then the solution was stirred for 3 hours at 100° C. under a nitrogen stream. The reaction solution was filtered, and the resultant product was then concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (14:100)), to thereby obtain the titled compound (39.4 mg, 79%).

Provenance & Evidence