tert-Butyldiphenylchlorosilane → HCID 178503852, compound

HRID 967331Notes

Reaction equation

HRID 967331 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([O:8][C@H:9]2[C@H:16]([OH:17])[C@@H:15]([CH2:18][OH:19])[O:14][C@@H:11]([S:12][CH3:13])[C@@H:10]2[NH:20][C:21](=[C:23]2[C:28](=[O:29])[CH2:27][C:26]([CH3:31])([CH3:30])[CH2:25][C:24]2=[O:32])[CH3:22])=[O:7])=[CH:4][CH:3]=1.[Si:35](Cl)([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C1C=CN=CC=1.ClCCCl.C(Cl)(Cl)Cl>[Si:35]([O:19][CH2:18][C@H:15]1[O:14][C@@H:11]([S:12][CH3:13])[C@H:10]([NH:20][C:21](=[C:23]2[C:24](=[O:32])[CH2:25][C:26]([CH3:31])([CH3:30])[CH2:27][C:28]2=[O:29])[CH3:22])[C@@H:9]([O:8][C:6](=[O:7])[C:5]2[CH:33]=[CH:34][C:2]([Cl:1])=[CH:3][CH:4]=2)[C@@H:16]1[OH:17])([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 2

HCID 94078tert-ButyldiphenylchlorosilaneHCID 178503850HCID 178503850, compound

Product 1

HCID 178503852HCID 178503852, compoundYield 75.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

A mixture of methyl 3-O-(p-chlorobenzoyl)-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-1-thio-β-D-glucopyranoside (3) (1.00 g, 1.95 mmol), t-butyldiphenylsilylchloride (536 mg, 1.95) and 4-dimethylaminopyridine (238 mg, 1.95 mmol), in 1,2-dichloroethane (30 mL), was stirred under reflux for 6 hours. The reaction mixture was cooled to room temperature, diluted with chloroform (60 mL) and washed with diluted brine (3×50 mL, brine/water, 1:2), dried over MgSO4. The solvent was removed in vacuo and the residue was chromatographed using hexane—EtOAc 1:1 as the mobile phase to give a white solid, methyl 6-O(t-butyldiphenylsilyl)-3-O-(p-chlorobenzoyl)-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-1-thio-β-D-glucopyranoside (4) (1.1 g, 75%).

Workup

  1. temperatureunder reflux for 6 hours
  2. washwashed with diluted brine (3×50 mL, brine/water, 1:2)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe residue was chromatographed

Sources & evidence

ORD record
ord-ea988490f9274ab7a6f4f3aa37d70ce4
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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