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

HRID 1016226ノート

反応式

HRID 1016226 の反応式
[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

参加物

5

反応物 2

HCID 7498Benzyl BromideHCID 10921145alpha-D-galactosyl fluoride

生成物 1

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

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cffac80fabff41b9adf82ecb8d529601
出典データセット
uspto-grants-2002_11
特許番号
US06475486B1

反応ノート

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