(5R,6R,6aR)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate → (5R,6R,6aR)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-6-ol
Reaktionsgleichung
CC1C=CC(S([O:11][C@H:12]2[C@@:16]3([CH3:22])[O:17][C:18]([CH3:21])([CH3:20])[O:19][CH:15]3[O:14][C@@H:13]2[CH2:23][O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=O)=O)=CC=1>C1COCC1>[Si:25]([O:24][CH2:23][C@H:13]1[O:14][CH:15]2[C@:16]([CH3:22])([O:17][C:18]([CH3:21])([CH3:20])[O:19]2)[C@@H:12]1[OH:11])([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The mixture of (5R,6R,6aR)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate (from step 4) (56 g, 0.094 mol) and 1M solution of Li(Et)3BH (376.4 mL, 0.376 mol) in 800 mL of THF was refluxed for 12 h. The reaction mixture was cooled to room temperature and quenched carefully with 200 mL of saturated ammonium chloride solution. Diluted with 500 mL of ethyl acetate and washed with 1N HCl (500 mL) and brine (300 mL). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was dissolved in ethyl acetate and passed through a pad of celite to remove salts. Purified by column chromatography using hexane and ethyl acetate as a gradient mixture to give 38.4 g of the title compound (93% yield).