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

HRID 429737

Reaction equation

HRID 429737 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d8b579bd8d7d4586a84888eaf75e694c
Source dataset
uspto-grants-2001_11
Patent number
US06319695B1

Linked notes

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