2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 90775216, compound

HRID 967343Notes

Reaction equation

HRID 967343 reaction equation
[N:1]([C@@H:4]1[C@@H:11]([O:12]CC2C=CC(OC)=CC=2)[C@H:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:9]([CH2:30][O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[O:8][C@H:5]1[S:6][CH3:7])=[N+:2]=[N-:3].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl.O>[N:1]([C@@H:4]1[C@@H:11]([OH:12])[C@H:10]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@@H:9]([CH2:30][O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[O:8][C@H:5]1[S:6][CH3:7])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 91513383HCID 91513383, compound

Product 1

HCID 90775216HCID 90775216, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

A mixture of methyl 2-azido-4-O-benzyl-6-O-(4-chlorobenzyl)-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D glucopyranoside (34) (580 mg, 1.01 mmol) and DDQ (270 mg, 1.2 mmol) in CH2Cl2—H2O 9:1 (10 mL) was stirred at room temperature for 3 hours. The reaction mixture was washed with saturated NaHCO3 solution (3×15 ml), dried over MgSO4 and evaporated. The residue was purified by chromatography using CHCl3-Hexane-MeOH 30:20:0.5 as the mobile phase to give methyl 2-azido-4-O-benzyl-6-O-(4-chlorobenzyl)-2-deoxy-1-thio-β-D glucopyranoside (35) (300 mg, 66%).

Workup

  1. washThe reaction mixture was washed with saturated NaHCO3 solution (3×15 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-56ea464152ab4e688c6f852087a0f623
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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