Trityl chloride → HCID 15432751, compound
Reaction equation
[S:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:19]1([C:25](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:19]1([C:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:12][CH2:11][C@H:9]2[O:10][C@@H:2]([S:1][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]2[OH:8])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Phenyl 1-thio-β-D-glucopyranoside (5) (7.01 g, 25.8 mmol) and triphenylmethyl chloride (9.33 g, 33.5 mmol) were suspended in pyridine (20 ml), and the mixture was refluxed for 5 hr. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate. The resulting solution was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; dichloromethane:ethyl acetate=1:1) to give phenyl 6-O-triphenylmethyl-1-thio-β-D-glucopyranoside (6) (13.1 g, yield 99%) as a white solid.