HRID1109266

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O

HCID36314

Paclitaxel

C47H51NO14

$结构：C/C=C(\C)C(=O)N[C@@H](c1ccccc1)[C@@H](O)C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C(=C1C)C2(C)C$

HCID6436208

未命名化合物

PRODUCTS

生成物

$结构：C/C=C(\C)C(=O)N[C@@H](c1ccccc1)[C@@H](O)C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C(=C1C)C2(C)C.CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O$

HCID86586153

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID345198

Platinic oxide

O2Pt

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

A 262 mg quantity of an approximately 50/50 mixture of taxol and cephalomannine was dissolved in 10 mL of ethyl acetate in a 100 mL round bottom flask with magnetic stirring. Then 20 mg of PtO2 was added and the flask was attached to a hydrogenation apparatus. After flushing the flask five times with hydrogen gas, the solution was stirred at room temperature. After 1 hour, the flask was removed from the hydrogenation apparatus and the solution filtered through Celite to remove the catalyst. The resulting solution was evaporated to dryness under vacuum. The result was 262 mg (100%) of a mixture of taxol and dihydrocephalomannine. No further purification was performed and the sample was used as is in the next step.

WORKUP

后处理

customAfter flushing the flask five times with hydrogen gas
customthe flask was removed from the hydrogenation apparatus
filtrationthe solution filtered through Celite
customto remove the catalyst
customThe resulting solution was evaporated to dryness under vacuum
customNo further purification

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a54f79637bfe4f938d92d89b1bc13c39
来源数据集: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05319112
来源说明: uspto-grants-1994_06

反应 SMILES

[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:40])[C@@H:24]([NH:31][C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6].[CH3:63]/[CH:64]=[C:65](/[C:67]([NH:69][C@H:70]([C@@H:77]([OH:122])[C:78]([O:80][C@@H:81]1[C:102]([CH3:103])=[C:101]2[C:104]([CH3:106])([CH3:105])[C@:83]([OH:121])([C@@H:84]([O:112][C:113]([C:115]3[CH:116]=[CH:117][CH:118]=[CH:119][CH:120]=3)=[O:114])[C@@H:85]3[C@:90]4([O:93][C:94]([CH3:96])=[O:95])[CH2:91][O:92][C@@H:89]4[CH2:88][C@H:87]([OH:97])[C@@:86]3([CH3:111])[C:98]([C@@H:100]2[O:107][C:108]([CH3:110])=[O:109])=[O:99])[CH2:82]1)=[O:79])[C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)=[O:68])\[CH3:66]>C(OCC)(=O)C.O=[Pt]=O>[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:40])[C@@H:24]([NH:31][C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6].[CH3:63]/[CH:64]=[C:65](/[C:67]([NH:69][C@H:70]([C@@H:77]([OH:122])[C:78]([O:80][C@@H:81]1[C:102]([CH3:103])=[C:101]2[C:104]([CH3:105])([CH3:106])[C@:83]([OH:121])([C@@H:84]([O:112][C:113]([C:115]3[CH:116]=[CH:117][CH:118]=[CH:119][CH:120]=3)=[O:114])[C@@H:85]3[C@:90]4([O:93][C:94]([CH3:96])=[O:95])[CH2:91][O:92][C@@H:89]4[CH2:88][C@H:87]([OH:97])[C@@:86]3([CH3:111])[C:98]([C@@H:100]2[O:107][C:108]([CH3:110])=[O:109])=[O:99])[CH2:82]1)=[O:79])[C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)=[O:68])\[CH3:66]