Methanol → Benzyl{(2R,3S)-3-hydroxy-4-[(tripropan-2-ylsilyl)oxy]butan-2-yl}carbamate

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Reaction Conditions

Reaction Steps

(5R,6S)-5,10-Dimethyl-3-oxo-1-phenyl-9,9-di(propan-2-yl)-2,8-dioxa-4-aza-9-silaundecan-6-yl 4-nitrobenzoate (7.90 g, 14.5 mmol) synthesized in Example (89c) was dissolved in methylene chloride (150 mL), and diisobutylaluminum hydride (1.0 mol/L hexane solution, 30.0 mL, 30.0 mmol) was added, followed by stirring at −40° C. for 8 hours under nitrogen atmosphere. The reaction solution was brought back to 0° C., and methanol (5.0 mL) was added, followed by addition of a 5N aqueous sodium hydroxide solution (150 mL), and extraction was carried out with methylene chloride (200 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=10%-15%) to afford the desired compound (3.70 g, yield 65%) as a colorless liquid.

Provenance & Evidence