Toluene → 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl chloride

HRID 842303Notes

Reaction equation

HRID 842303 reaction equation
C(O[C@@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[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)C.[Al+3].[Cl-:29].[Cl-].[Cl-].C1(C)C=CC=CC=1.[Si](O)(O)(O)O>C(Cl)(Cl)Cl>[CH3:26][C:25]([O:24][CH2:23][C@H:21]1[O:22][C@@H:5]([Cl:29])[C@H:6]([O:7][C:8]([CH3:9])=[O:10])[C@@H:11]([O:12][C:13]([CH3:14])=[O:15])[C@@H:16]1[O:17][C:18]([CH3:19])=[O:20])=[O:27]

Participants

6

Reactant 4

HCID 1140TolueneHCID 14942Orthosilicic acidHCID 2724702beta-D-Glucose pentaacetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 109595272,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of β-D-glucose pentaacetate (20 g) in CHCl3 (100 mL) was added AlCl3 (3.6 g). After stirring at room temperature, toluene (100 mL) was added, followed by silicic acid (2 g). The mixture was stirred for a few minutes and the precipitate was removed by filtration. The solution was partially concentrated under vacuum and extracted with ice cold water (25 mL). The organic phase was concentrated to a syrupy mixture and ether was added to precipitate acetochloro-β-D-glucose as a powder (12 g).

Workup

  1. stirringThe mixture was stirred for a few minutes
  2. customthe precipitate was removed by filtration
  3. concentrationThe solution was partially concentrated under vacuum
  4. extractionextracted with ice cold water (25 mL)
  5. concentrationThe organic phase was concentrated to a syrupy mixture and ether
  6. additionwas added
  7. customto precipitate acetochloro-β-D-glucose as a powder (12 g)

Sources & evidence

ORD record
ord-1852d66a299b432399841ac1a344b597
Source dataset
uspto-grants-2002_04
Patent number
US06372895B1

Reaction notes

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