[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[H][H].S(C1C=CC(C)=CC=1)(O)(=O)=O.S(C1C=CC(C)=CC=1)(O)(=O)=O.O[CH2:39][C@H:40]1[CH2:44][CH2:43][C@@H:42]([CH2:45]O)[O:41]1>CN(C)C=O>[CH2:12]([O:11][C:3]([C:4]1([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:45][CH:42]2[O:41][CH:40]([CH2:44][CH2:43]2)[CH2:39]1)=[O:10])[CH3:13]Sodium hydride (2.28 grams, 95 mmole) is added in portions to a stirred solution of diethyl malonate (15 mL, 99 mmole) in N,N-dimethylformamide (400 mL). The mixture is stirred for 45 minutes at which time evolution of hydrogen is complete. A solution of cis-2,5-bis(hydroxymethyl)tetrahydrofuran ditosylate (19.0 grams, 43 mmole) in N,N-dimethylformamide (400 mL) is then added dropwise. The mixture is heated in an oil bath at 140° C. overnight. After cooling to room temperature, the mixture was quenched by addition of saturated aqueous ammonium chloride solution and concentrated under vacuum. The residual oil is taken up in water and extracted with diethyl ether. The organic extract is washed with water and brine, dried over magnesium sulfate and concentrated to an oil.
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