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

HRID 610441Notes

Reaction equation

HRID 610441 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][OH:39])[O:18][CH:10]1[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[N:42]([C:45]1[CH:52]=[CH:51][C:48]([CH2:49]Br)=[CH:47][C:46]=1[Cl:53])=[N+:43]=[N-:44].O>CN(C=O)C>[N:42]([C:45]1[CH:52]=[CH:51][C:48]([CH2:49][O:39][CH2:38][C@H:19]2[O:18][CH:10]([S:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:20]2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:47][C:46]=1[Cl:53])=[N+:43]=[N-:44]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 114820004-Azido-3-chlorobenzyl bromideHCID 54027025Phenyl 2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside

Product 1

HCID 11354530Phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzyl-1-thio-D-glucopyranosideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenyl 2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside (3) (1.09 g, 2.00 mmol) in DMF (10 ml) was added sodium hydride (60% in oil, 96 mg, 2.40 mmol), and the resulting mixture was stirred at room temperature for 15 min. The reaction mixture was cooled to 0° C. and 4-azido-3-chlorobenzyl bromide (592 mg, 2.40 mmol) was added, which was followed by stirring at room temperature for 4 hr. Water (30 ml) was added and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with 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=5:1) to give phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside (4) (1.33 g, yield 94%) as slightly yellow crystals.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringby stirring at room temperature for 4 hr
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-baf9956c10ff45dd9d3ad2545077ee52
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

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