1,3,5-Benzenetrisulfonyl trichloride → Benzene 1,3,5-trisulfonyl trisglucosamine

HRID 1112196Notes

Reaction equation

HRID 1112196 reaction equation
C([O:4][CH:5]1[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]([O:9]C(=O)C)[C@H:6]1[NH2:7])(=O)C.[C:25]1([S:39](Cl)(=[O:41])=[O:40])[CH:30]=[C:29]([S:31](Cl)(=[O:33])=[O:32])[CH:28]=[C:27]([S:35](Cl)(=[O:37])=[O:36])[CH:26]=1>C(#N)C.N1C=CC=CC=1>[C:25]1([S:39]([C:5]2([O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]([OH:9])[C@H:6]2[NH2:7])[OH:4])(=[O:41])=[O:40])[CH:30]=[C:29]([S:31]([C:5]2([O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]([OH:9])[C@H:6]2[NH2:7])[OH:4])(=[O:33])=[O:32])[CH:28]=[C:27]([S:35]([C:5]2([O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]([OH:9])[C@H:6]2[NH2:7])[OH:4])(=[O:37])=[O:36])[CH:26]=1

Participants

4

Reactant 2

HCID 889401,3,5-Benzenetrisulfonyl trichlorideHCID 13059363glucosamine tetra-O-acetate

Product 1

HCID 131711300Benzene 1,3,5-trisulfonyl trisglucosamine

Reagents, catalysts & solvents 1

HCID 21959178Acetonitrile pyridineSolvent

Procedure

The novel intermediate benzene 1,3,5-trisulfonyl trisglucosamine compound is prepared by reacting tetra-O-acetyl glucosamine (II) with 1,3,5-benzenetrisulfonyl chloride in a weakly basic polar medium such as acetonitrile-pyridine for 24 hours. The solvent is concentrated and the tetraacetyl trisulfonyl derivative (III) is precipitated from ice water and extracted into methylene dichloride. The solvent is evaporated and the material is dissolved in cold methanol saturated with ammonia. Standing in the cold for 24 hours, followed by the addition of nitrogen gas to remove ammonia, produces a thick oil (IV) on evaporation. The oil is purified from water with activated charcoal, filtration and drying to give the intermediate glucopyranose.

Workup

  1. customfor 24 hours
  2. concentrationThe solvent is concentrated
  3. customthe tetraacetyl trisulfonyl derivative (III) is precipitated from ice water
  4. extractionextracted into methylene dichloride
  5. customThe solvent is evaporated
  6. dissolutionthe material is dissolved in cold methanol saturated with ammonia
  7. customcold for 24 hours
  8. additionfollowed by the addition of nitrogen gas
  9. customto remove ammonia

Sources & evidence

ORD record
ord-c013e7efacb043df979dc2d420b9b549
Source dataset
uspto-grants-1978_10
Patent number
US04120953

Reaction notes

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