2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 23396149, compound

HRID 967346Notes

Reaction equation

HRID 967346 reaction equation
[N:1]([C@@H:4]1[C@@H:11]([O:12]CC2C=CC(OC)=CC=2)[C@H:10]([O:22][C:23]([C:25]2[C:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@@H:9]([CH2:37][O:38][Si:39]([C:52]([CH3:55])([CH3:54])[CH3:53])([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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][C:23]([C:25]2[C:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@@H:9]([CH2:37][O:38][Si:39]([C:52]([CH3:55])([CH3:54])[CH3:53])([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=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 23396150HCID 23396150, compound

Product 1

HCID 23396149HCID 23396149, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

A mixture of methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-62-D-glucopyranoside (11) (150 mg, 0.19 mmol) and DDQ (52 mg, 0.23 mmol) in CH2Cl2—H2O 9:1 (5 mL) was stirred at room temperature for 3 hours. The reaction mixture was washed with saturated NaHCO3 solution (3×3 ml), dried over MgSO4 and evaporated. The residue was purified by chromatography using EtOAc—hexane 15:85 as the mobile phase to give methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside (41) (116 mg, 92%).

Workup

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

Sources & evidence

ORD record
ord-2e2c372e5bc74c87acdc8de4e6ad0564
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

Loading…