Sodium hydride → methyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzyl-D-glucopyranoside

HRID 610440Notes

Reaction equation

HRID 610440 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:14]([CH2:33][OH:34])[O:13][CH:10]1[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[N:37]([C:40]1[CH:47]=[CH:46][C:43]([CH2:44]Br)=[CH:42][C:41]=1[Cl:48])=[N+:38]=[N-:39]>CN(C=O)C>[N:37]([C:40]1[CH:47]=[CH:46][C:43]([CH2:44][O:34][CH2:33][C@H:14]2[O:13][CH:10]([O:11][CH3:12])[C@H:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:16]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C@@H:15]2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:42][C:41]=1[Cl:48])=[N+:38]=[N-:39]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11454061Methyl 2,3,4-tri-O-benzyl-D-glucopyranosideHCID 114820004-Azido-3-chlorobenzyl bromide

Product 1

HCID 15433383methyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzyl-D-glucopyranosideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (1.16 g, 2.5 mmol) was dissolved in DMF (10 ml) and thereto was added sodium hydride (60% in oil, 120 mg, 3.00 mmol) at 0° C., followed by stirring for 15 min. Then 4-azido-3-chlorobenzyl bromide (740 mg, 3.00 mmol) was added portionwise. The resulting mixture was stirred at 0° C. for 30 min and at room temperature for 3 hr. Ice-water was added and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to give the title compound as a yellow oil (1.48 g, yield 94%).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 30 min and at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1a6df0db42c04a68bf40e90086a29680
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

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