Tetrabutylammonium Fluoride → methyl 2,3,4-tri-O-benzyl-beta-D-glucopyranoside
Reaction equation
[Si]([O:18][CH2:19][C@H:20]1[O:27][C@@H:24]([O:25][CH3:26])[C@H:23]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:22]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:21]1[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[CH2:29]([O:28][C@@H:23]1[C@@H:22]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C@H:21]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C@@H:20]([CH2:19][OH:18])[O:27][C@H:24]1[O:25][CH3:26])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside (2.81 g, 3.98 mmol) in dry THF (40 ml, 0.1 M) at room temperature was added tetrabutyl ammonium fluoride (4.37 ml, 4.37 mmol, 1 M solution in THF). After stirring for 3 hours, the reaction solution was diluted with ethyl acetate (300 ml) and washed with water (1×100 ml) and saturated aqueous NaCl (1×100 ml), and dried with magnesium sulfate. Concentration and flash chromatography (silica, 50% ether in petroleum ether) provided pure target compound (1.62 g, 88%) as a white solid.
Workup
- washwashed with water (1×100 ml) and saturated aqueous NaCl (1×100 ml)
- dry with materialdried with magnesium sulfate
- concentrationConcentration and flash chromatography (silica, 50% ether in petroleum ether)
Sources & evidence
- ORD record
- ord-24c954d5ed724ce3a03f8b5fbc6e375a
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06197963B1
Reaction notes
Loading…