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

HRID 610445Notes

Reaction equation

HRID 610445 reaction equation
[N:1]([C:4]1[CH:55]=[CH:54][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]CC3C=CC(OC)=CC=3)[C@@H:13]([O:34]CC3C=CC(OC)=CC=3)[C@@H:12]2[O:44]CC2C=CC(OC)=CC=2)=[CH:6][C:5]=1[Cl:56])=[N+:2]=[N-:3].O.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.O=C1O[C@H]([C@H](CO)O)C(O)=C1O>ClCCl>[N:1]([C:4]1[CH:55]=[CH:54][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:34])[C@@H:12]2[OH:44])=[CH:6][C:5]=1[Cl:56])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15433387Phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-(4-methoxybenzyl)-1-thio-beta-D-glucopyranosideHCID 54670067L-Ascorbic Acid

Product 1

HCID 54482702Phenyl 6-O-(4-azido-3-chlorobenzyl)-1-thio-beta-D-glucopyranosideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (9) (1.24 g, 1.55 mmol) in dichloromethane (10 ml) were added water (0.5 ml) and DDQ (1.41 g, 6.21 mmol), and the resulting mixture was stirred at room temperature for 3 hr. Thereto was added 5% aqueous L-ascorbic acid solution, and the mixture was stirred for a while, and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution 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; dichloromethane:ethyl acetate=1:3) to give phenyl 6-O-(4-azido-3-chlorobenzyl)-1-thio-β-D-glucopyranoside (10) (584 mg, yield 86%) as yellow crystals.

Workup

  1. stirringthe mixture was stirred for a while
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent; dichloromethane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-3524a53505d044a9b9b43dca15108622
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

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