Hydrochloric Acid → 1,5-Anhydro-2-azido-6-O-[tert-butyl(dimethyl)silyl]-2,3-dideoxy-D-xylo-hexitol

Temperature

-78 °C

Lithium tri-sec-butylborohydride/tetrahydrofuran solution (1.0 mol/l, 0.83 ml, 0.83 mmol) was added to a tetrahydrofuran (2.5 ml) solution of the compound (169 mg, 0.59 mmol) obtained in Step 1 above at −78° C. and the resulting mixture was stirred at −78° C. for 45 minutes. 1N hydrochloric acid was added, the resulting mixture was subjected to extraction with ethyl acetate and the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=20:1→12:1 (v/v)] to give 101 mg (59%) of the title compound as a colorless oil.

1. extractionthe resulting mixture was subjected to extraction with ethyl acetate
2. washthe organic layer was washed with brine
3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
4. customthe solvent was evaporated under reduced pressure
5. customthe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=20:1→12:1 (v/v)]

ORD record

ord-4ac0f7ff711e43ebb6e19be1cd291fe5

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629133B2