alpha-D-Glucopyranosyl bromide, tetraacetate → 2,3,4,6-Tetra-O-acetylglucopyranosylisothiocyanate

HRID 970299Notes

Reaction equation

HRID 970299 reaction equation
[S-:1][C:2]#[N:3].[K+].[C:5]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:11][C@@H:10]1Br)(=[O:7])[CH3:6]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[C:5]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:11][C@H:10]1[N:3]=[C:2]=[S:1])(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 516872Potassium thiocyanate

Product 1

HCID 994622,3,4,6-Tetra-O-acetylglucopyranosylisothiocyanateYield 76%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent2×

Procedure

Potassium thiocyanate (2.81 g, 28.7 mmol), tetrabutylammonium hydrogen sulphate (1.22 g, 3.59 mmol) and molecular sieves (6.00 g) were stirred in absolute acetonitrile (500 ml) for 30 minutes. 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 37 (5.90 g, 14.4 mmol) was then dissolved in acetonitrile, added to the reaction flask and refluxed for 90 minutes. The solution was then allowed to cool, filtered through a celite pad and concentrated. Purification by column chromatography in hexane:ethyl acetate 2:1 (v/v) to give 52 (4.26 g, 76%).

Workup

  1. additionadded to the reaction flask
  2. temperaturerefluxed for 90 minutes
  3. temperatureto cool
  4. filtrationfiltered through a celite pad
  5. concentrationconcentrated
  6. customPurification by column chromatography in hexane:ethyl acetate 2:1 (v/v)

Sources & evidence

ORD record
ord-27cf8f96066d45c4b21924b4c0ac827f
Source dataset
uspto-grants-2007_12
Patent number
US07312194B2

Reaction notes

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