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Hydrochloric Acid → 1,2,4,6-Tetra-o-acetyl-3-deoxy-3-(3,5-dimethoxybenzamido)-d-galactopyranose

HRID 1869606
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1869606
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86613986[(2R,3R,4S,5R)-3,5,6-Triacetoxy-4-azido-tetrahydropyran-2-YL]methyl acetate

Produkt 1

HCID 674050501,2,4,6-Tetra-o-acetyl-3-deoxy-3-(3,5-dimethoxybenzamido)-d-galactopyranoseAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938
Palladium
Katalysator
HCID 702EthanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-186a3ee2f23548469587c979c49869c5
Quelldatensatz
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07638623B2

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