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

HRID 2056319

반응식

HRID 2056319 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6c9ca79f8a2140b4b43df5383739ecf2
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335500B2

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