Benzoyl chloride → 1,2,3,4-Tetra-O-benzoyl-L-fucose

HRID 2056319

Reaktionsgleichung

Reaktionsgleichung von HRID 2056319
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:10]=[CH:11][C@H:12]([C@@H:14]([C@@H:16]([C@H:18]([CH3:20])[OH:19])[OH:17])[OH:15])[OH:13]>N1C=CC=CC=1>[CH3:20][C@@H:18]1[O:19][CH:11]([O:10][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])[C@@H:12]([O:13][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])[CH:14]([O:15][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])[C@H:16]1[O:17][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Komponenten

4

Edukt 2

HCID 7412Benzoyl chlorideHCID 3034656L-(-)-Fucose

Produkt 1

HCID 717524001,2,3,4-Tetra-O-benzoyl-L-fucose

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Benzoyl chloride (21.4 g, 152.3 mmol; 17.7 mL) was added dropwise to a cooled solution of L-fucose (5.0 g, 30.5 mmol) in pyridine (100 mL), at 0-5° C., and the mixture was stirred for three hours at room temperature. The mixture was poured onto ice water and extracted with ethyl acetate (EtOAc). The extracts were successively washed with ice cold dilute HCl, aqueous NaHCO3, and brine, dried over anhydrous MgSO4, and concentrated. The product was used for the next step without further purification.

Aufarbeitung

  1. additionThe mixture was poured onto ice water
  2. extractionextracted with ethyl acetate (EtOAc)
  3. washThe extracts were successively washed with ice cold dilute HCl, aqueous NaHCO3, and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe product was used for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-6c9ca79f8a2140b4b43df5383739ecf2
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335500B2

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