HRID1695839

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID944

Nitric Acid

HNO3

结构：CC(=O)OC[C@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc(O)cc3)c2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

HCID67115824

未命名化合物

PRODUCTS

生成物

结构：CC(=O)OC[C@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc(O)c([N+](=O)[O-])c3)c2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

HCID67115761

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID74236

未命名化合物

溶剂HCID6365

1,1-Dichloroethane

C2H4Cl2

PROCEDURE

实验过程

To a stirred solution of compound prepared in step I (2 g, 3.64 mmol) in dichloroethane (20 mL) was added TBAB (117 mg, 0.364 mmol), 6% aqueous nitric acid (20 mmol) at 0-5° C. and stirred at room temperature for 4 h. Organic layer was separated, washed with water and brine and concentrated to furnish crude acetic acid (2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-(4-hydroxy-3-nitro-benzyl)-phenyl]-tetrahydro-pyran-2-ylmethyl ester which was further purified by column chromatography (1.5 g)

WORKUP

后处理

customOrganic layer was separated
washwashed with water and brine
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d3de69818edb408e857fc151aa5ca9c9
来源数据集: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08163704B2
来源说明: uspto-grants-2012_04

反应 SMILES

[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2].[N+:39]([O-])([OH:41])=[O:40]>ClC(Cl)C.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[C:31]([N+:39]([O-:41])=[O:40])[CH:32]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:34][O:35][C:36](=[O:38])[CH3:37])(=[O:3])[CH3:2]