Water → Phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-(4-methoxybenzyl)-1-thio-beta-D-glucopyranoside

HRID 610444Notes

Reaction equation

HRID 610444 reaction equation
[CH3:1][O:2][C:3]1[CH:45]=[CH:44][C:6]([CH2:7][O:8][C@@H:9]2[C@@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C@H:20]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[C@@H:19]([CH2:42][OH:43])[O:18][C@H:10]2[S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[N:46]([C:49]1[CH:56]=[CH:55][C:52]([CH2:53]Br)=[CH:51][C:50]=1[Cl:57])=[N+:47]=[N-:48].[H-].[Na+].O>CN(C=O)C>[N:46]([C:49]1[CH:56]=[CH:55][C:52]([CH2:53][O:43][CH2:42][C@H:19]2[O:18][C@@H:10]([S:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:9]([O:8][CH2:7][C:6]3[CH:44]=[CH:45][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C@@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C@@H:20]2[O:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=2)=[CH:51][C:50]=1[Cl:57])=[N+:47]=[N-:48]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 114820004-Azido-3-chlorobenzyl bromideHCID 15433386Phenyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-beta-D-glucopyranoside

Product 1

HCID 15433387Phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-(4-methoxybenzyl)-1-thio-beta-D-glucopyranosideYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (8) (1.25 g, 1.98 mmol) and 4-azido-3-chlorobenzyl bromide (584 mg, 2.37 mmol) in DMF (10 ml) was added sodium hydride (60% in oil, 95 mg, 2.37 mmol), and the resulting mixture was stirred at room temperature for 3 hr. Cold water was added and the mixture was extracted twice with ether. The combined ether layers were 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; hexane:ethyl acetate=4:1) to give phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (9) as white crystals (1.25 g, yield 79%).

Workup

  1. extractionthe mixture was extracted twice with ether
  2. washThe combined ether layers were washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-43b604fd80b34958b88a63bb8a57dd36
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

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