HRID482672

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8212

Octadecanoyl chloride

C18H35ClO

HCID8471

Triethylamine

C6H15N

反应SMILES：CCCCCCCCCCCCCCCCCCN(C(=O)CC(=O)CCC(=O)CCCC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

HCID18601735

未命名化合物

HCID21881414

未命名化合物

PRODUCTS

产物

反应SMILES：CCCCCCCCCCCCCCCCCCC(O)[C@H]1O[C@@H](N(CCCCCCCCCCCCCCCCCC)C(=O)CC(=O)CCC(=O)CCCC)[C@H](O)[C@@H](O)[C@@H]1O

HCID57223674

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

CONDITIONS

反应条件

温度: 20 °C

PROCEDURE

实验过程

1.2 g (0.004 mol) of octadecanoyl chloride and 2.0 g (0.0034 mol) of N-octadecyl-N-3,6-dioxodecanoyl-β-D-glucopyranosylamine in 50 ml of tetrahydrofuran are initially taken, and 0.4 g of triethylamine (0.004 mol) is added at 0° C. The mixture is stirred for 1 day at 20° C., the solid is filtered off with suction and the solvent is removed in a water-pump vacuum. The residue is chromatographed on a column containing 250 g of silica gel, using as mobile phase 10:1 toluene/isopropanol, and 1.9 g (65% of theory) of N-octadecyl-N-3,6-dioxodecoyl-(6-stearyl-β-D-glucopyranosyl)-amine are obtained, having an Rf value of 0.296 (6:1 toluene/isopropanol).

WORKUP

后处理

filtrationthe solid is filtered off with suction
customthe solvent is removed in a water-pump vacuum
customThe residue is chromatographed on a column
additioncontaining 250 g of silica gel
customare obtained

来源与证据

来源类型: Open Reaction Database
ORD记录: ord-f4f4056478cb463eb5459611a675ae7e
来源数据集: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US04574122
来源说明: uspto-grants-1986_03

反应SMILES

[C:1](Cl)(=O)[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][CH2:16][CH2:17][CH3:18].[CH2:21]([N:39]([C@@H:53]1[O:61][C@H:60]([CH2:62][OH:63])[C@@H:58]([OH:59])[C@H:56]([OH:57])[C@H:54]1[OH:55])[C:40](=[O:52])[CH2:41][C:42](=[O:51])[CH2:43][CH2:44][C:45](=[O:50])[CH2:46][CH2:47][CH2:48][CH3:49])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C(N(CC)CC)C.C1(C)C=CC=CC=1.C(O)(C)C>O1CCCC1>[CH2:21]([N:39]([C@@H:53]1[O:61][C@H:60]([CH:62]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[OH:63])[C@@H:58]([OH:59])[C@H:56]([OH:57])[C@H:54]1[OH:55])[C:40](=[O:52])[CH2:41][C:42](=[O:51])[CH2:43][CH2:44][C:45](=[O:50])[CH2:46][CH2:47][CH2:48][CH3:49])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]