Trimethylsilyl triflate → 1-allyl-1-deoxy-2,3,4-tri-O-benzyl-alpha-L-fucopyranose

HRID 1721010노트

반응식

HRID 1721010 반응식
[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:13]([CH3:32])[O:12]C1O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([Si](C)(C)C)[CH:34]=[CH2:35].[CH3:40][Si](OS(C(F)(F)F)(=O)=O)(C)C>C(#N)C>[CH2:34]([C@@H:35]1[O:12][C@@H:13]([CH3:32])[C@@H:14]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:9]1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:33]=[CH2:40]

참가 물질

5

반응물 3

HCID 65367Trimethylsilyl triflateHCID 69808AllyltrimethylsilaneHCID 2734155(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

생성물 1

HCID 153448101-allyl-1-deoxy-2,3,4-tri-O-benzyl-alpha-L-fucopyranose수율 79%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 2,3,4-tri-O-benzyl-L-fucopyranose (11a, 10.0 g) in acetonitrile (100 ml) at 0° C., allyltrimethylsilane (12 ml) was added followed by trimethylsilyltrifluoromethanesulfonate (14.5 ml). The solution was warmed to room temperature and was stirred for 14 hours at room temperature. The mixture was quenched with water (100 ml) in an ice-water bath. The acetonitrile was evaporated in vacuo and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with saturated sodium carbonate solution, followed by saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude mixture was eluted on a silica gel column (150 ml, hexane:ethyl acetate, 10:1) to provide 1-allyl-1-deoxy-2,3,4-tri-O-benzyl-α-L-fucopyranose (11b, 9.2 g, 79%).

후처리

  1. customThe mixture was quenched with water (100 ml) in an ice-water bath
  2. customThe acetonitrile was evaporated in vacuo
  3. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  4. washThe combined organic extracts were washed with saturated sodium carbonate solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe crude mixture was eluted on a silica gel column (150 ml, hexane:ethyl acetate, 10:1)

출처 및 근거

ORD 기록
ord-7977dd6953534378beaf585df6c9a2f8
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05508387

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