tert-Butyldiphenylchlorosilane → HCID 12114350, compound
Reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:19]([C@@H:22]1[C@@H:29]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[C@@H:28]([OH:40])[C@@H:27]([CH2:41][OH:42])[O:26][C@H:23]1[S:24][CH3:25])=[N+:20]=[N-:21]>CN(C)C1C=CN=CC=1.ClCCCl.C(Cl)(Cl)Cl>[N:19]([C@@H:22]1[C@@H:29]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[C@@H:28]([OH:40])[C@@H:27]([CH2:41][O:42][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:26][C@H:23]1[S:24][CH3:25])=[N+:20]=[N-:21]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
A mixture of t-butyldiphenylsilyl chloride (151 mg, 0.54 mmol), 4-dimethylaminopyridine (90 mg, 0.73 mmol) and methyl 2-azido-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside (15) (130 mg, 0.36 mmol) in dry 1,2-dichloroethane (8 mL) was stirred at 80° C. for 2 hours. The resulting clear solution was cooled to room temperature, diluted with CHCl3 (20 mL), washed with H2O (3×20 mL), brine solution (20 mL), dried over MgSO4 and evaporated. The residue was purified by chromatography using hexane—ether 2:1 as the mobile phase to give methyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside (16) (142 mg, 68%).
Workup
- temperatureThe resulting clear solution was cooled to room temperature
- washwashed with H2O (3×20 mL), brine solution (20 mL)
- dry with materialdried over MgSO4
- customevaporated
- customThe residue was purified by chromatography
Sources & evidence
- ORD record
- ord-a1cc5488b84f44369d72241db89ca687
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06953850B1
Reaction notes
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