Acetic Anhydride → 7-O-(Triethylsilyl) Baccatin III

HRID 619703

反応式

HRID 619703 の反応式
[CH2:1]([Si:3](Cl)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:9][C:10]1[C@@H:27]([OH:28])[CH2:26][C@:22]2([OH:29])[C:23]([CH3:25])([CH3:24])[C:11]=1[C@@H:12]([OH:47])[C:13]([C@@:15]1([CH3:46])[C@H:20]([C@@H:21]2[O:30][C:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:32])[C@:19]2([O:41][C:42]([CH3:44])=[O:43])[CH2:39][O:40][C@@H:18]2[CH2:17][C@@H:16]1[OH:45])=[O:14].[C:48](OC(=O)C)(=[O:50])[CH3:49]>N1C=CC=CC=1>[CH3:2][CH2:1][Si:3]([O:45][C@@H:16]1[C@@:15]2([CH3:46])[C:13]([C@H:12]([O:47][C:48]([CH3:49])=[O:50])[C:11]3[C:23]([CH3:24])([CH3:25])[C@:22]([OH:29])([C@@H:21]([O:30][C:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:32])[C@@H:20]2[C@:19]2([O:41][C:42]([CH3:44])=[O:43])[CH2:39][O:40][C@@H:18]2[CH2:17]1)[CH2:26][C@H:27]([OH:28])[C:10]=3[CH3:9])=[O:14])([CH2:6][CH3:7])[CH2:4][CH3:5]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 13819ChlorotriethylsilaneHCID 15427210-deacetylbaccatin III

生成物 1

HCID 99399277-O-(Triethylsilyl) Baccatin III収率 77%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
5 °C

実験手順

182 g of triethylsilyl chloride are added over 1 hour 20 minutes to a solution of 293.9 g of 10-deacetylbaccatin III in 2.7 liters of pyridine. The solution obtained is stirred for 40 hours at 5° C. 360 g of acetic anhydride are then added while the temperature is maintained at 5° C. The suspension obtained is stirred for 48 hours at 20° C. and then poured into 40 liters of ice-cold water. The precipitate obtained is separated by filtration, then washed with 8 times 2 liters of water and lastly dissolved in 3 liters of ethyl acetate. The organic phase is dried over magnesium sulphate. After filtration and concentration under reduced pressure, the product obtained is crystallized in isopropyl ether. 7-(Triethylsilyl)baccatin III is thereby obtained in a 77% yield, the characteristics of which product are as follows:

後処理

  1. customThe solution obtained
  2. temperatureis maintained at 5° C
  3. customThe suspension obtained
  4. stirringis stirred for 48 hours at 20° C.
  5. customThe precipitate obtained
  6. customis separated by filtration
  7. washwashed with 8 times 2 liters of water
  8. dissolutionlastly dissolved in 3 liters of ethyl acetate
  9. dry with materialThe organic phase is dried over magnesium sulphate
  10. filtrationAfter filtration and concentration under reduced pressure
  11. customthe product obtained
  12. customis crystallized in isopropyl ether

出典と根拠

ORDレコード
ord-64b6443b641f4ba481be1bfbe1569598
出典データセット
uspto-grants-1999_09
特許番号
US05959125

関連ノート

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