Hydrogen Bromide → 2,3,4-Tri-O-Acetyl-6-Deoxy-alpha-D-Glucopyranosyl Bromide

HRID 433869

反応式

HRID 433869 の反応式
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH3:11])[OH:10])[OH:8])[OH:6])[OH:4].[BrH:12]>C(O)(=O)C.ClCCl>[C:3]([O:10][C@@H:9]1[C@@H:7]([O:8][C:5](=[O:6])[CH3:7])[C@H:5]([O:6][C:9](=[O:10])[CH3:11])[C@@H:3]([CH3:2])[O:4][C@@H:11]1[Br:12])(=[O:4])[CH3:2]

参加物

5

反応物 2

HCID 260Hydrogen BromideHCID 935796-Deoxyglucose

生成物 1

HCID 128982142,3,4-Tri-O-Acetyl-6-Deoxy-alpha-D-Glucopyranosyl Bromide収率 85.4%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

In a 10 mL round bottom flask containing 10 mL of glacial acetic acid was placed 6-deoxyglucose (332.3 mg) and the reaction was cooled to 0° C. Hydrobromic acid in glacial acetic acid (5 mL of a 30 wt. % solution) was added dropwise. The reaction was stirred for 4 hours. The reaction was diluted with 100 mL of dichloromethane and washed with 50 mL ice water and then 50 mL of cold saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate and filtered. The solvent was removed in vacuo to yield the title compound as a yellow solid (636.5 mg, 85.4%) and the product was used without further purification as in Example 1. MS (FAB) calculated for C12H17O7Br (M−Br) 273.1, found 273.1.

後処理

  1. washwashed with 50 mL ice water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-da861d3f276d4fffaed66d8205cdf948
出典データセット
uspto-grants-2003_12
特許番号
US06670324B2

関連ノート

読み込み中…