HRID619703

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7918

Acetic anhydride

C4H6O3

HCID13819

Silane, chlorotriethyl-

C6H15ClSi

结构：CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@@]1(C)C(=O)[C@H](O)C3=C(C)[C@@H](O)C[C@@](O)([C@@H](OC(=O)c4ccccc4)[C@H]21)C3(C)C

HCID154272

10-Deacetylbaccatin III

C29H36O10

PRODUCTS

生成物

结构：CC[Si](CC)(CC)O[C@H]1C[C@H]2OC[C@@]2(OC(C)=O)[C@H]2[C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](O)C(C)=C([C@@H](OC(C)=O)C(=O)[C@]12C)C3(C)C

HCID9939927

7-O-(Triethylsilyl) Baccatin III

C37H52O11Si

收率 77%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1049

Pyridine

C5H5N

CONDITIONS

反应条件

温度: 5 °C

PROCEDURE

实验过程

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:

WORKUP

后处理

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

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-64b6443b641f4ba481be1bfbe1569598
来源数据集: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05959125
来源说明: uspto-grants-1999_09

反应 SMILES

[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]