反応式
[O:1]([CH3:13])[C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@@H:3]1[OH:4].CO[CH:16](OC)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28](S(O)(=O)=O)=[CH:27][CH:26]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[CH3:13][O:1][C@H:2]1[O:10][C@@H:9]2[CH2:11][O:12][CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C@H:7]2[C@@H:5]2[O:6][CH:35]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:4][C@H:3]12参加物
実験手順
A mixture of methyl α-D-mannopyranoside (Compound I, 50 g, 258 mmoles), α,α-dimethoxytoluene (92 g, 600 mmoles), and anhydrous p-toluene-sulfonic acid (1 g) in N,N-dimethylformamide (300 ml), in a 1-liter flask fitted with an air condenser attached to a water aspirator, was stirred magnetically and heated in an oil bath for 3 hours at 65°-75° C. None of the starting Compound I remained after this time (t.l.c., 4:1 ether-petroleum ether). The mixture was poured with vigorous stirring into 1 liter of ice-water containing sodium hydrogen carbonate (30 g). The resultant precipitate was filtered off, resuspended in ice-water, filtered off again, and dried in air and finally in vacuo over phosphorus pentaoxide; yield 90.6 g (95%), m.p. 120°-160° C, [α]D23 -33° (c 1, chloroform).
後処理
- customin a 1-liter flask fitted with an air condenser
- temperatureheated in an oil bath for 3 hours at 65°-75° C
- additionThe mixture was poured
- filtrationThe resultant precipitate was filtered off
- filtrationfiltered off again
- dry with materialdried in air and finally in vacuo over phosphorus pentaoxide
出典と根拠
- ORDレコード
- ord-a2d4f6e2d6c24c4ea620abc8d54369cb
- 出典データセット
- uspto-grants-1977_05
- 特許番号
- US04024333
関連ノート
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