Sodium Iodide → HCID 13833585, compound

HRID 430446Notes

Reaction equation

HRID 430446 reaction equation
[C:1]([O:4][C@@H:5]1[O:22][C@H:21]([CH2:23]S(C)(=O)=O)[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].[I-:28].[Na+]>C(C(C)=O)C>[C:1]([O:4][C@@H:5]1[O:22][C@H:21]([CH2:23][I:28])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 54392295HCID 54392295, compound

Product 1

HCID 13833585HCID 13833585, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A 1 L round bottom flask containing 500 mL of methyl ethyl ketone was charged with 1,2,3,4-tetra-O-acetyl-6-deoxy-6-methanesulfonyl-β-D-glucopyranose (4.45 g, 10.44 mmol) and sodium iodide (15.73 g, 104.9 mmol). The reaction was heated at reflux for 24 hours. The solvent was removed in vacuo and the resulting residue was taken up in 250 mL dichloromethane. The organic layer was washed with sodium thiosulfate (2×100 mL), water (2×100 mL) and once with 100 mL of brine. The organic layer was dried over magnesium sulfate, filtered and the solvent removed in vacuo to yield crude 1,2,3,4-tetra-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranose as a white solid (4.99 g) which was used directly in Preparation 4.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was removed in vacuo
  4. washThe organic layer was washed with sodium thiosulfate (2×100 mL), water (2×100 mL) and once with 100 mL of brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-648a230410c447fbaf429370c35dc27c
Source dataset
uspto-grants-2001_11
Patent number
US06323176B1

Reaction notes

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