Water → HCID 58786170, compound

HRID 1375980Notes

Reaction equation

HRID 1375980 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH3:11].[CH2:12]([O:19][C@@H:20]1[C@@H:32]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:31]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@@H:30]([CH2:49][O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[O:29][C@@H:21]1OC(=O)C(F)(F)F)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C(Cl)Cl>[CH2:12]([O:19][C@@H:20]1[C@@H:32]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:31]([O:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C@@H:30]([CH2:49][O:50][CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[O:29][C@H:21]1[C:6]1[CH:7]=[C:2]([Br:1])[C:3]([O:10][CH3:11])=[CH:4][C:5]=1[O:8][CH3:9])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 872661-Bromo-2,4-dimethoxybenzeneHCID 12900825HCID 12900825, compound

Product 1

HCID 58786170HCID 58786170, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-bromo-2,4-dimethoxybenzene (9.1 ml) was added to a solution of 2,3,4,6-tetra-O-benzyl-1-O-(trifluoroacetyl)-α-D-glucopyranose (20.0 g) in methylene chloride (100 ml) and the mixture was stirred for 10 minutes. Boron trifluoride-diethyl ether complex (3.9 ml) was added to the reaction mixture and the mixture was stirred at room temperature for 12 hours. Water was added to the reaction mixture and the mixture was extracted with methylene chloride. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-(5-bromo-2,4-dimethoxyphenyl)-D-glucitol (17.0 g).

Workup

  1. additionBoron trifluoride-diethyl ether complex (3.9 ml) was added to the reaction mixture
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2e84938df7fa4ad38b1834bfbd2099b9
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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