Pyridine → HCID 18642954, compound

HRID 703616Notes

Reaction equation

[Si:1]([O:8][C:9]([C:11]([F:27])([F:26])[C@H:12]([C@@H:14]([CH:16]([C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:17])[OH:15])[OH:13])=[O:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CC=CC=1.[F:34][C:35]([F:48])([F:47])[S:36]([O:39]S(C(F)(F)F)(=O)=O)(=[O:38])=[O:37]>ClCCl>[Si:1]([O:8][C:9]([C:11]([F:26])([F:27])[C@:12]([O:39][S:36]([C:35]([F:48])([F:47])[F:34])(=[O:38])=[O:37])([C@@H:14]([CH:16]([C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:17])[OH:15])[OH:13])=[O:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -20 °C

Procedure

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).

Workup

temperatureto maintain the temperature between -5° and -20° C
temperatureto warm to room temperature
washwas washed with saturated aqueous sodium bicarbonate
dry with materialThe remaining organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3fafbeadaa524dd6bb89cd0ad8843741
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04983724

Reaction notes

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