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

HRID 2056319

反応式

HRID 2056319 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6c9ca79f8a2140b4b43df5383739ecf2
出典データセット
uspto-grants-2008_02
特許番号
US07335500B2

関連ノート

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