Pyridine → HCID 18642954, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.3 gm (5.9 mMol) 1-t-butyldimethylsilyloxy-5-benzoyl-2-deoxy-2,2-difluoroxylose in dichloromethane (100 mL) were added 7.2 mL (88.5 mMol) pyridine and the reaction mixture was cooled to -20° C. To this was then added a solution of 1.5 mL (8.9 mMol) trifluoromethanesulfonic anhydride in dichloromethane (20 mL) dropwise at such a rate as to maintain the temperature between -5° and -20° C. The reaction mixture was stirred for 40 minutes at -15° C. The reaction mixture was then allowed to warm to room temperature and was washed with saturated aqueous sodium bicarbonate. The remaining organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 2.8 gm (90%) of the desired compound as a yellow oil. FD-MS: m/e=463(M-57, loss of t-butyl).

Provenance & Evidence