Trifluoromethanesulfonic anhydride → Methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranoside

Temperature

-78 °C

To a stirred solution of methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside (800 mg, 1.71 mmol) in 8.55 mL of dry dichloromethane at -78° C. was added 2,6-di-tert-butyl-4-methyl pyridine (632 mg, 3.08 mmol) followed by triflic anhydride (345 μl, 2.05 mmol). After stirring 15 minutes at -78° C., the mixture was warmed to room temperature over 20 minutes, and then poured into a solution of saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (50 mL) . The organic layer was washed with saturated NaHCO3 (3×20 mL), saturated aqueous NaCl (1×20 mL), and dried over magnesium sulfate. Concentration provided crude target compound, which was used in the next step without further purification.

1. temperaturethe mixture was warmed to room temperature over 20 minutes
2. extractionextracted with ethyl acetate (50 mL)
3. washThe organic layer was washed with saturated NaHCO3 (3×20 mL), saturated aqueous NaCl (1×20 mL)
4. dry with materialdried over magnesium sulfate
5. concentrationConcentration
6. customprovided crude target compound, which
7. customwas used in the next step without further purification

ORD record

ord-64e624400a8044a4945c9a1191bbb478

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05811512