反応式
[C:1]([O:4][CH2:5][C@H:6]1[O:15][CH:10]([O:11]C(=O)C)[C@H:9]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:8]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:7]1[Cl:34])(=[O:3])[CH3:2].C(O)(=O)C.NN>CN(C=O)C>[C:1]([O:4][CH2:5][C@H:6]1[O:15][CH:10]([OH:11])[C@H:9]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:8]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:7]1[Cl:34])(=[O:3])[CH3:2]参加物
実験手順
A solution of acetyl 6-O-acetyl-2,3-di-O-benzoyl-4-chloro-4-deoxy-D-galactopyranoside (68) (8.53 g, 17.4 mmol) and hydrazine acetate (2.4 g, 26.0 mmol, 1.5 eq) in 70 mL of DMF was stirred for 1 hour at room temperature. The reaction mixture was then evaporated, washed with water (5 times) and evaporated. The residue was chromatographed on a silica gel, eluting with hexane-ethyl acetate (2:1), to provide 6-O-acetyl-2,3-di-O-benzoyl-4-chloro-4-deoxy-D-galactopyranose (7.44 g, 95.3%). This material was dissolved in dichloromethane (50 mL) and the resulting solution was cooled to 0° C. Trichloroacetonitrile (8.3 mL, 82.9 mmol) was added and the mixture was stirred for 2 hours. The solvent was then evaporated and the residue was chromatographed on a silica gel column, eluting with hexane-ethyl acetate (3:1), to give imidate 69 (6.3 g, 64%).
後処理
- customThe reaction mixture was then evaporated
- washwashed with water (5 times)
- customevaporated
- customThe residue was chromatographed on a silica gel
- washeluting with hexane-ethyl acetate (2:1)
出典と根拠
- ORDレコード
- ord-6a72c4319da943fd86dd2ca0bdbc31d5
- 出典データセット
- uspto-grants-1999_02
- 特許番号
- US05874411
関連ノート
読み込み中…