HRID576433

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7841

Allyl bromide

C3H5Br

HCID11430

Potassium Carbonate

CK2O3

结构：CCOc1ccc(Cc2cc(C3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c(O)c(Br)c2Cl)cc1

HCID86714094

未命名化合物

PRODUCTS

生成物

结构：C=CCOc1c(C2O[C@H](COCc3ccccc3)[C@@H](OCc3ccccc3)[C@H](OCc3ccccc3)[C@H]2OCc2ccccc2)cc(Cc2ccc(OCC)cc2)c(Cl)c1Br

HCID86714093

未命名化合物

收率 62.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID180

Acetone

C3H6O

溶剂HCID516892

Sodium Bicarbonate

CHNaO3

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

To a solution of 2-bromo-3-chloro-4-(4-ethoxybenzyl)-6-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenol (500 mg, 0.579 mmole) in acetone (15 mL) were added K2CO3 (120 mg, 0.869 mmole) and allyl bromide (75 μL, 0.869 mmole) continuously. The resulting solution was stirred at 60° C. overnight, diluted with a saturated NaHCO3 and extracted with ethyl acetate. The organic layer was washed with water then brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the title compound (325 mg, 62%) as a colorless gum.

WORKUP

后处理

extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialbrine, dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified on Biotage® purification apparatus

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a5ff867272a94f3cb18d8e3884171ad1
来源数据集: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09034921B2
来源说明: uspto-grants-2015_05

反应 SMILES

[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH:19]2[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:20]2)[C:3]=1[OH:58].C([O-])([O-])=O.[K+].[K+].[CH2:65](Br)[CH:66]=[CH2:67]>CC(C)=O.C([O-])(O)=O.[Na+]>[CH2:67]([O:58][C:3]1[C:2]([Br:1])=[C:7]([Cl:8])[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)=[CH:5][C:4]=1[CH:19]1[C@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:22]([O:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[O:20]1)[CH:66]=[CH2:65]