Dimethyl Sulfate → HCID 70212997, compound
Reaction equation
[CH3:1][N:2]([CH3:19])[C@H:3]1[CH2:16][C@@H:15]([CH3:17])[O:14][CH:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:4]1[OH:18].[H-].[Na+].[CH3:22]OS(OC)(=O)=O>O1CCCC1.C(OCC)(=O)C.O>[CH3:22][O:18][C@@H:4]1[C@@H:3]([N:2]([CH3:1])[CH3:19])[CH2:16][C@@H:15]([CH3:17])[O:14][CH:5]1[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
Procedure
Benzyl 3,4,6-trideoxy-3-(dimethylamino)-D-xylohexopyranoside (Korte, F., A. Bilow and R. Heinz, Tetrahedron, 1962, 18, 657,666, 10.01 g, 38.06 mmoles) was dissolved in tetrahydrofuran (300 mL) with stirring at room temperature under an argon atmosphere. The solution was treated with small portions of sodium hydride (60% oil dispersion, 1.83 g, 45.68 mmoles). After one hour, dimethylsulfate (5.28 g, 41.87 mmoles) was added and the reaction mixture was stirred for two hours. The reaction mixture was quenched by the careful addition of water and the solution was evaporated in vacuo leaving an-oily residue which was resuspended in ethyl acetate and water. The organic layer was separated, dried (MgSO4) and filtered to afford 9.74 g (93%) of the title compound as a slightly yellow oil which solidified on standing.
Workup
- stirringthe reaction mixture was stirred for two hours
- customThe reaction mixture was quenched by the careful addition of water
- customthe solution was evaporated in vacuo
- customleaving an-oily residue which
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-f9cf39aeb89246e3bc065796428e74c0
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05563135
Reaction notes
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