HRID1155300

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8471

Triethylamine

C6H15N

结构：CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](S)O[C@H](CN2C(=O)c3ccccc3C2=O)[C@@H]1OC(C)=O

HCID12805522

未命名化合物

结构：CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OCCCCCCI)CC[C@]4(C)[C@H]3CC[C@]12C

HCID12805525

未命名化合物

PRODUCTS

生成物

结构：CC(=O)O[C@H]1[C@@H](OC(C)=O)[C@@H](CN2C(=O)c3ccccc3C2=O)O[C@@H](SCCCCCCO[C@H]2CC[C@@]3(C)C(=CC[C@H]4[C@@H]5CC[C@H]([C@H](C)CCCC(C)C)[C@@]5(C)CC[C@@H]43)C2)[C@@H]1OC(C)=O

HCID131712555

未命名化合物

收率 78.6%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

Triethylamine (0.8 ml.) is added to a solution of 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranose (2.5 g.) and 6-(5-cholesten-3β-yloxy)hexyl iodide (3.3 g.) in dichloromethane (20 ml.). The solution is kept at room temperature under nitrogen overnight, and washed with water, dried, and evaporated in vacuo to a syrup (4.71 g.). This material is put on a column of silica gel and eluted with chloroform followed by 2% ethyl acetate in chloroform. The desired fractions are combined and evaporated in vacuo to give the title compound (4.0 g., 78%); Rf 0.2 (CHCl3 -EtOAc. 95:5), [α]D27 -93° C. (C 1.18, chloroform); n.m.r. (chloroform-d); δ 7.60-7.91 (4 aromatic), 1.93, 2.03, and 2.24 (3 OAc) 0.68 (CH3 -18).

WORKUP

后处理

washwashed with water
customdried
customevaporated in vacuo to a syrup (4.71 g.)
washeluted with chloroform
customevaporated in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7cb8033918014cd99e35e259fcefb0e9
来源数据集: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04301152
来源说明: uspto-grants-1981_11

反应 SMILES

C(N(CC)CC)C.[C:8]([O:11][C@@H:12]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]([O:23][C:24](=[O:26])[CH3:25])[C@@H:16]([CH2:27][N:28]2[C:32](=[O:33])[C:31]3=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]3[C:29]2=[O:38])[O:15][C@H:13]1[SH:14])(=[O:10])[CH3:9].[CH3:39][CH:40]([CH2:42][CH2:43][CH2:44][C@H:45]([C@@H:47]1[C@:64]2([CH3:65])[C@H:50]([C@H:51]3[C@H:61]([CH2:62][CH2:63]2)[C@:59]2([CH3:60])[C:54]([CH2:55][C@@H:56]([O:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72]I)[CH2:57][CH2:58]2)=[CH:53][CH2:52]3)[CH2:49][CH2:48]1)[CH3:46])[CH3:41]>ClCCl>[C:8]([O:11][C@@H:12]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]([O:23][C:24](=[O:26])[CH3:25])[C@@H:16]([CH2:27][N:28]2[C:32](=[O:33])[C:31]3=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]3[C:29]2=[O:38])[O:15][C@H:13]1[S:14][CH2:72][CH2:71][CH2:70][CH2:69][CH2:68][CH2:67][O:66][C@H:56]1[CH2:57][CH2:58][C@@:59]2([CH3:60])[C:54](=[CH:53][CH2:52][C@@H:51]3[C@@H:61]2[CH2:62][CH2:63][C@@:64]2([CH3:65])[C@H:50]3[CH2:49][CH2:48][C@@H:47]2[C@H:45]([CH3:46])[CH2:44][CH2:43][CH2:42][CH:40]([CH3:41])[CH3:39])[CH2:55]1)(=[O:10])[CH3:9]