Benzyl Bromide → 2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride

HRID 1294441

반응식

HRID 1294441 반응식
[C@H:1]1([F:12])[O:9][C@H:8]([CH2:10][OH:11])[C@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.[Ag]=O>[CH2:13]([O:3][C@@H:2]1[C@@H:4]([O:5][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:6]([O:7][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:8]([CH2:10][O:11][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:9][C@@H:1]1[F:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 2

HCID 7498Benzyl BromideHCID 10921145alpha-D-galactosyl fluoride

생성물 1

HCID 99590292,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride

시약·촉매·용매 2

HCID 92152Silver(II) oxide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
-20 °C

실험 절차

α-D-galactopyranosyl fluoride (2.30 g, 12.62 mmol) was dissolved in dry DMF (40 ml) and, at −20° C., benzyl bromide (12.95 g, 75.72 mmol) and silver oxide (10 g) were added. The reaction mixture was stirred at −20° C. for 5 h and then at room temperature for 24 h. The salts were then filtered off and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel (350 g) with 15:1 petroleum ether/ethyl acetate.

후처리

  1. waitat room temperature for 24 h
  2. filtrationThe salts were then filtered off
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (350 g) with 15:1 petroleum ether/ethyl acetate

출처 및 근거

ORD 기록
ord-75f8de51bba34535985917060252b27d
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241595B2

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