Hydrochloric Acid → D-Galactopyranose, 3-deoxy-3-[(3,5-dimethoxybenzoyl)amino]-, 1,2,4,6-tetraacetate

HRID 1869606Notes

Reaction equation

HRID 1869606 reaction equation
[C:1]([O:4][CH:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([N:24]=[N+]=[N-])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].Cl.[CH2:28]([O:30][CH2:31][CH3:32])C>C(O)C.[Pd]>[C:1]([O:4][CH:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:11]([NH:24][C:17](=[O:18])[C:12]2[CH:32]=[C:31]([O:30][CH3:28])[CH:5]=[C:6]([O:7][CH3:8])[CH:11]=2)[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86613986HCID 86613986, compound

Product 1

HCID 67405050D-Galactopyranose, 3-deoxy-3-[(3,5-dimethoxybenzoyl)amino]-, 1,2,4,6-tetraacetateYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-D-galactopyranose 1 (167 mg, 0.45 mmol) was suspended in ethanol (5 ml), and palladium (10% on carbon, 17 mg) and HCl (1 ml of a 1M solution in diethyl ether) were added. The mixture was degassed and stirred at room temperature under a hydrogen atmosphere. After 1 h, dichloromethane was added, and the mixture was filtered through Celite and concentrated in vacuo. Half of the residue was dissolved in dichloromethane (2 ml) and pyridine (0.5 ml). 3,5-Dimethoxybenzoyl chloride (168 mg) was added, and the mixture was stirred at room temperature. After 18 h, TLC (1:1, heptane:ethyl acetate) showed the presence of a single carbohydrate product (Rf 0.2). The reaction mixture was diluted with diethyl ether (30 ml) and washed with H2SO4 (30 ml of a 10% aqueous solution), NaHCO3 (30 ml of a saturated aqueous solution), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography to give 1,2,4,6-tetra-O-acetyl-3-deoxy-3-(3,5-dimethoxybenzamido)-D-galactopyranose 4 (50 mg, 44%).

Workup

  1. customThe mixture was degassed
  2. additiondichloromethane was added
  3. filtrationthe mixture was filtered through Celite
  4. concentrationconcentrated in vacuo
  5. dissolutionHalf of the residue was dissolved in dichloromethane (2 ml)
  6. addition3,5-Dimethoxybenzoyl chloride (168 mg) was added
  7. stirringthe mixture was stirred at room temperature
  8. waitAfter 18 h
  9. additionThe reaction mixture was diluted with diethyl ether (30 ml)
  10. washwashed with H2SO4 (30 ml of a 10% aqueous solution), NaHCO3 (30 ml of a saturated aqueous solution)
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-186a3ee2f23548469587c979c49869c5
Source dataset
uspto-grants-2009_12
Patent number
US07638623B2

Reaction notes

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