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

HRID 610446Notes

Reaction equation

HRID 610446 reaction equation
[N:1]([C:4]1[CH:28]=[CH:27][C:7]([CH2:8][O:9][CH2:10][C@H:11]2[O:23][C@@H:15]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:14]([OH:24])[C@@H:13]([OH:25])[C@@H:12]2[OH:26])=[CH:6][C:5]=1[Cl:29])=[N+:2]=[N-:3].[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[OH2:39]>N1C=CC=CC=1>[N:1]([C:4]1[CH:28]=[CH:27][C:7]([CH2:8][O:9][CH2:10][C@H:11]2[O:23][C@@H:15]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:14]([O:24][C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@@H:13]([O:25][C:8](=[O:39])[C:7]3[CH:27]=[CH:28][CH:4]=[CH:5][CH:6]=3)[C@@H:12]2[O:26][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:6][C:5]=1[Cl:29])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 54482702Phenyl 6-O-(4-azido-3-chlorobenzyl)-1-thio-beta-D-glucopyranoside

Product 1

HCID 11308693Phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzoyl-1-thio-beta-D-glucopyranoside

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of phenyl 6-O-(4-azido-3-chlorobenzyl)-1-thio-β-D-glucopyranoside (10) (580 mg, 1.32 mmol) in pyridine (5 ml) was added benzoyl chloride (609 μl, 5.28 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 2 hr. Thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (11) as slightly yellow crystals (934 mg, yield 94%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-805e86d9cc7a4cbfa841d0328a519962
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

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