HRID1937722

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8206

Hexadecanoyl chloride

C16H31ClO

结构：NCCC(=O)N(C(=O)OCC1c2ccccc2-c2ccccc21)[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O

HCID68661469

未命名化合物

PRODUCTS

生成物

结构：CCCCCCCCCCCCCCCC(=O)C(O)[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@H](N(C(=O)CCN)C(=O)OCC2c3ccccc3-c3ccccc32)[C@@]1(O)C(=O)CCCCCCCCCCCCCCC

HCID86587671

未命名化合物

收率 65%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1049

Pyridine

C5H5N

PROCEDURE

实验过程

Palmitoyl chloride (1.55 mL, 1.8 mmol) was added to a solution of nucleoside 28 in abs pyridine and the reaction mixture was stirred overnight at room temperature. The solution was then quenched with MeOH, evaporated to dryness, dissolved in dichloromethane and washed with saturated aq sodium bicarbonate and brine. The organic phase was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica (EtOAc-Hexanes 1:1) affording 0.5 g of 29 (yield, 65%).

WORKUP

后处理

customThe solution was then quenched with MeOH
customevaporated to dryness
dissolutiondissolved in dichloromethane
washwashed with saturated aq sodium bicarbonate and brine
dry with materialThe organic phase was dried over sodium sulfate
customevaporated to dryness
customThe residue was purified by flash chromatography on silica (EtOAc-Hexanes 1:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6cdfd17635bb413b89901a5e8c450467
来源数据集: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06395713B1
来源说明: uspto-grants-2002_05

反应 SMILES

[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:19]([N:36]([C@@H:42]1[C@H:46]([OH:47])[C@@H:45]([CH2:48][OH:49])[O:44][C@H:43]1[N:50]1[CH:57]=[CH:56][C:54](=[O:55])[NH:53][C:51]1=[O:52])[C:37](=[O:41])[CH2:38][CH2:39][NH2:40])([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20]>N1C=CC=CC=1>[C:1]([C@@:46]1([OH:47])[C@@H:45]([CH:48]([C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[OH:49])[O:44][C@@H:43]([N:50]2[CH:57]=[CH:56][C:54](=[O:55])[NH:53][C:51]2=[O:52])[C@@H:42]1[N:36]([C:19]([O:21][CH2:22][CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[C:35]1=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:20])[C:37](=[O:41])[CH2:38][CH2:39][NH2:40])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]