HRID1885424

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC

HCID2241

未命名化合物

HCID7937

2,6-Dimethylpyridine

C7H9N

结构：CC(C)[Si](OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C

HCID2724529

Triisopropylsilyl trifluoromethanesulfonate

C10H21F3O3SSi

PRODUCTS

生成物

结构：CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O[Si](C(C)C)(C(C)C)C(C)C)C(OC)C3)C(C)C(O[Si](C(C)C)(C(C)C)C(C)C)CC1=O)C(C)CC2OC

HCID57200842

未命名化合物

收率 94%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8058

n-Hexane

C6H14

CONDITIONS

反应条件

温度: 0 °C

PROCEDURE

实验过程

A stirred solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (7.0 g, 8.84 mmol) containing 2,6 lutidine (3.7 g, 34.6 mmol) was cooled to 0° C. and treated with triisopropylsilyl trifluoromethanesulfonate (11.06 g, 36.0 mmol). After stirring at RT for 16 hr, the reaction mixture was diluted with n-hexane (400 ml). The suspension was filtered and the filtrate passed over SiO2 (760 g). Elution with n-hexane/ethyl acetate (3:1) yielded 17-ethyl-1-hydroxy-14-triisopropylsilyloxy-12-[2'-(4"-triisopropylsilyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (9.18 g, 94%) as a foam. Mass Spec (C61H109NO12Si2)(1104.72) FAB+Li:1110 (M+Li), 745, 720, 695, 266.

WORKUP

后处理

filtrationThe suspension was filtered
washElution with n-hexane/ethyl acetate (3:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-42631b8819e346d0a11e41909e362ff6
来源数据集: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05143918
来源说明: uspto-grants-1992_09

反应 SMILES

[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([OH:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([OH:55])[CH2:5][C:4]1=[O:56])[CH3:2].N1[C:62]([CH3:63])=[CH:61]C=CC=1C.FC(F)(F)S(O[Si:71]([CH:78]([CH3:80])[CH3:79])([CH:75]([CH3:77])[CH3:76])[CH:72]([CH3:74])[CH3:73])(=O)=O>CCCCCC>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:50][Si:71]([CH:78]([CH3:80])[CH3:79])([CH:75]([CH3:77])[CH3:76])[CH:72]([CH3:74])[CH3:73])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([O:55][Si:71]([CH:62]([CH3:61])[CH3:63])([CH:75]([CH3:77])[CH3:76])[CH:72]([CH3:74])[CH3:73])[CH2:5][C:4]1=[O:56])[CH3:2]