HRID1820605

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID23669913

未命名化合物

结构：C=CCOC(=O)[C@@H]1O[C@@H](Oc2ccc([N+](=O)[O-])cc2C2OCCO2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C

HCID68983558

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C(=O)O)O[C@@H](Oc2ccc([N+](=O)[O-])cc2C2OCCO2)[C@@H]1O[Si](C)(C)C(C)(C)C

HCID68982700

未命名化合物

收率 100.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID7858

Allyl alcohol

C3H6O

2 次

CONDITIONS

反应条件

温度: 50 °C

PROCEDURE

实验过程

The solution of 5.64 g (7.58 mmol) of the compound, presented according to Example LE3d, in 150 ml of allyl alcohol is mixed with 9.1 ml of a 1 M solution of sodium allyl alcoholate in allyl alcohol, and it is stirred for 2.5 hours at 50° C. It is concentrated by evaporation, mixed with water, extracted several times with dichloromethane, the combined organic extracts are washed with saturated sodium chloride solution and dried on magnesium sulfate. The residue that is obtained after filtration and removal of the solvent is purified by chromatography on fine silica gel, and 1.78 g (2.44 mmol, 32%) of the title compound as well as 1.87 g (2.43 mmol, 32%) of (2R,3S,4S,5R,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(2-[1,3]dioxolan-2-yl-4-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid allyl ester are isolated.

WORKUP

后处理

concentrationIt is concentrated by evaporation
additionmixed with water
extractionextracted several times with dichloromethane
washthe combined organic extracts are washed with saturated sodium chloride solution
customdried on magnesium sulfate
customThe residue that is obtained
filtrationafter filtration and removal of the solvent

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-23b623758f31488d8f71058893e410fc
来源数据集: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07605136B2
来源说明: uspto-grants-2009_10

反应 SMILES

C([O-])C=C.[Na+].C([O:9][C:10]([C@H:12]1[C@H:17]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@H:16]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C@@H:15]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[C@H:14]([O:42][C:43]2[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][C:44]=2[CH:52]2[O:56][CH2:55][CH2:54][O:53]2)[O:13]1)=[O:11])C=C>C(O)C=C>[C:22]([Si:19]([CH3:21])([CH3:20])[O:18][C@@H:17]1[C@H:16]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C@@H:15]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:36])[CH3:37])[C@H:14]([O:42][C:43]2[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][C:44]=2[CH:52]2[O:56][CH2:55][CH2:54][O:53]2)[O:13][C@@H:12]1[C:10]([OH:11])=[O:9])([CH3:23])([CH3:24])[CH3:25]