Ammonia → HCID 21961224, compound

Participants

Reaction Steps

4.1 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.

Provenance & Evidence