HRID1943577

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COc1ccc(-c2oc3c(CC=C(C)C)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cc(O)c3c(=O)c2O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)cc1

HCID5318997

Icariin

C33H40O15

HCID10942334

Methanol, sodium salt

CH3NaO

PRODUCTS

生成物

结构：COc1ccc(-c2oc3c(CC=C(C)C)c(O)cc(O)c3c(=O)c2O)cc1

HCID5318980

Icaritin

C21H20O6

结构：COc1ccc(-c2oc3c(CC=C(C)C)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cc(O)c3c(=O)c2O)cc1

HCID5745470

Baohuoside-1

C27H30O11

结构：COc1ccc(-c2oc3c(CC=C(C)C)c(O)cc(O)c3c(=O)c2O[C@@H]2O[C@H](C)[C@@H](O)[C@H](O)[C@@H]2O)cc1

HCID44587252

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1049

Pyridine

C5H5N

CONDITIONS

反应条件

温度: 80 °C

PROCEDURE

实验过程

20 g of the extract prepared in Example 1 was taken in dry pyridine (500 ml) and sodium methoxide (powder, 10 g) was added thereto. The solution was heated to reflux in a water bath at 80° C. for 8 hours to hydrolyze sugars bonded to icariin. The reaction was concentrated under pressure to remove the solvent. The residue was added to ethanol (200 ml), stirred (3 times) and subjected to filtration to remove precipitated salts. The filtrate was concentrated under pressure to obtain a crude product, which was then separated by silica gel column chromatography (chloroform:methanol=8:1 to 4:1) to give 0.6 g of icaritin, 0.7 g of icariside 1 and 0.8 g of icariside II.

WORKUP

后处理

temperatureThe solution was heated
concentrationThe reaction was concentrated under pressure
customto remove the solvent
additionThe residue was added to ethanol (200 ml)
filtrationsubjected to filtration
customto remove
customprecipitated salts
concentrationThe filtrate was concentrated under pressure
customto obtain a crude product, which
customwas then separated by silica gel column chromatography (chloroform:methanol=8:1 to 4:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-575a8382b4a746aab3ea7feeb32a2ece
来源数据集: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08394775B2
来源说明: uspto-grants-2013_03

反应 SMILES

C[O-].[Na+].[CH3:4][C@@H:5]1[O:10][C@@H:9]([O:11][C:12]2[C:21](=[O:22])[C:20]3[C:19]([OH:23])=[CH:18][C:17]([O:24][C@@H:25]4[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@H:27]([OH:34])[C@H:26]4[OH:35])=[C:16]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[C:15]=3[O:14][C:13]=2[C:41]2[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)[C@H:8]([OH:49])[C@H:7]([OH:50])[C@H:6]1[OH:51]>N1C=CC=CC=1>[CH3:39][C:38]([CH3:40])=[CH:37][CH2:36][C:16]1[C:15]2[O:14][C:13]([C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=3)=[C:12]([OH:11])[C:21](=[O:22])[C:20]=2[C:19]([OH:23])=[CH:18][C:17]=1[OH:24].[CH3:39][C:38]([CH3:40])=[CH:37][CH2:36][C:16]1[C:15]2[O:14][C:13]([C:41]3[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=3)=[C:12]([OH:11])[C:21](=[O:22])[C:20]=2[C:19]([OH:23])=[CH:18][C:17]=1[O:24][C@@H:25]1[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@H:27]([OH:34])[C@H:26]1[OH:35].[CH3:4][C@H:5]1[O:10][C@@H:9]([O:11][C:12]2[C:21](=[O:22])[C:20]3[C:19]([OH:23])=[CH:18][C:17]([OH:24])=[C:16]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[C:15]=3[O:14][C:13]=2[C:41]2[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)[C@@H:8]([OH:49])[C@@H:7]([OH:50])[C@@H:6]1[OH:51]