Dimethylformamide → HCID 21362959, compound

HRID 1169011Notes

Reaction equation

HRID 1169011 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1Br)(=[O:3])[CH3:2].[CH3:25][S:26](=[S:29])([O-:28])=[O:27].[Na+].CN(C=O)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:25][S:26](=[S:29])([O:28][C@@H:6]1[O:7][C@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:5]1[O:4][C:1](=[O:3])[CH3:2])=[O:27]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24436Sodium SulfateHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate2×HCID 23688755Methanesulfonothioic acid, sodium salt

Product 1

HCID 21362959HCID 21362959, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Procedure

2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide (1 g, 2.44 mmol) and sodium methanethiosulfonate (0.4 g, 3.05 mmol) were placed under nitrogen. 30 ml of anhydrous toluene was added followed by tetrabutylammonium bromide (69 mg, 0.21 mmol) and the mixture heated under reflux for 75 minutes. Part way through 6 ml of DMF were added as it seemed that 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide was insoluble in toluene. Reaction continued to reflux despite the fact that solution not formed. Thin Layer Chromatography (“TLC”) at end of reaction showed reaction to have gone to completion. Solution reduced on high pressure rotary evaporator to remove DMF. Product purified on flash silica gel column, reaction mixture added directly onto column (adding a small amount of Celite to reaction mixture sufficient to avoid salt cake forming on top of column.) Petroleum Ether: Ethyl Acetate 60:40 was used as the eluting solvent. Yield=75%.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 75 minutes
  3. customReaction
  4. temperatureto reflux despite the fact that solution not
  5. customformed
  6. customThin Layer Chromatography (“TLC”) at end of reaction
  7. customreaction
  8. customSolution reduced on high pressure rotary evaporator
  9. customto remove DMF
  10. customProduct purified on flash silica gel column, reaction mixture
  11. additionadded directly onto column (
  12. additionadding a small amount of Celite
  13. customto reaction mixture sufficient

Sources & evidence

ORD record
ord-c5aa2762da0e4d8f9bba42fcb7424456
Source dataset
uspto-grants-2003_09
Patent number
US06627744B2

Reaction notes

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