Acetone → HCID 13833585, compound

HRID 1362775Notes

Reaction equation

HRID 1362775 reaction equation
C1(C)C=CC(S(O[CH2:11][C@H:12]2[O:21][C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:15]([O:22][C:23](=[O:25])[CH3:24])[C@@H:14]([O:26][C:27](=[O:29])[CH3:28])[C@@H:13]2[O:30][C:31](=[O:33])[CH3:32])(=O)=O)=CC=1.CC(C)=O.[I-:39].[Na+]>O>[I:39][CH2:11][C@H:12]1[O:21][C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:15]([O:22][C:23](=[O:25])[CH3:24])[C@@H:14]([O:26][C:27](=[O:29])[CH3:28])[C@@H:13]1[O:30][C:31](=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 14214839HCID 14214839, compound

Product 1

HCID 13833585HCID 13833585, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-O-(p-Toluenesulfonyl)-1,2,3,4-tetra-O-acetyl-β-D-glucose (5, 18.5 g, 36.8 mmol) was place in a 500-mL round-bottomed flask. Acetone (200 ml) and sodium iodide (18.5 g, 123 mmol) were added. The resulting mixture was heated at reflux for 20 h. The reaction proceeded gradually. The mixture was poured into 1000 ml of water, and the resulting solid was filtered with a glass filter. Recrystalization from ethanol afforded 6-deoxy-6-iodo-1,2,3,4-tetra-O-acetyl-β-D-glucose (compound 6) in 65% yield (11.0 g, 24.0 mmol).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 20 h
  3. filtrationthe resulting solid was filtered with a glass
  4. filtrationfilter
  5. customRecrystalization from ethanol

Sources & evidence

ORD record
ord-ead0be12f63c472ab020cdbcb426ab5e
Source dataset
uspto-grants-2011_02
Patent number
US07883687B2

Reaction notes

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