[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[O:16][CH:17]2[CH:22]([OH:23])[CH:21]([OH:24])[CH:20]([OH:25])[CH:19]([CH2:26][OH:27])[O:18]2)=[O:10])=[CH:5][CH:4]=1.[BH4-].[Na+].ClCCl.CO.N>O1CCCC1.CO.O>[OH:10][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:11]1[S:12][CH:13]=[CH:14][C:15]=1[O:16][CH:17]1[CH:22]([OH:23])[CH:21]([OH:24])[CH:20]([OH:25])[CH:19]([CH2:26][OH:27])[O:18]14.1 g of (4-methoxy-phenyl)-[3-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-thiophen-2-yl]-methanone were dissolved in 200 ml of tetrahydrofuran+20 ml of methanol, and 500 mg of sodium borohydride were added. After the reaction was complete (TLC check, dichloromethane/methanol/conc. ammonia=30:5:0.1; about 30-60 min), water was added and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated. 2-{2-[Hydroxy-(4-methoxy-phenyl)-methyl]-thiophen-3-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol was obtained as crude product which was purified by filtration through silica gel.
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