Hydrochloric Acid → (2R,3R,4S,5S,6R)-2-[3-[[4-(3-benzyloxypropoxy)phenyl]-hydroxy-methyl]-4-methyl-indol-1-yl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

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Reaction Steps

To a 0.5 L stirred round bottom flask, purged with nitrogen, charge [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[4-(3-benzyloxypropoxy)benzoyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (12.33 mmol), THF (50 mL), and ethanol (100 mL). Add sodium tetrahydroborate (37.0 mmol) and stir at room temperature for 6 hours. Acidify by dropwise addition of 5N HCl then dilute with water (200 mL) and dichloromethane (200 mL). Separate the organics and wash with brine (200 mL). Dry over sodium sulphate, filter, and concentrate to give the title compound as a mixture of diastereomers in sufficient purity to be used without further purification in the next step (7.2 g crude) mass spectrum (m/z): 546.4 (M+1-18).

Provenance & Evidence