(2S,5R,6R,8R,10R)-10-[(1S,2R,3R,5R,7S)-2-(tert-butyldimethylsilyl)oxy-7-[(1R,2S)-1-[(2S,3R)-4-(tert-butyldimethylsilyl)oxy-2,3-dimethylbutyl]-4-(tert-butyldiphenylsilyl)oxymethyl-1-(1-trimethylsilyloxybut-3-enyl)cyclohex-3-en-2-yl]-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-2-(2-propynyl)-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecane | 1075244-26-6

分子结构分类

有机化合物 - 有机杂环化合物 - 氧杂环己烷

中文名称

——

中文别名

——

英文名称

(2S,5R,6R,8R,10R)-10-[(1S,2R,3R,5R,7S)-2-(tert-butyldimethylsilyl)oxy-7-[(1R,2S)-1-[(2S,3R)-4-(tert-butyldimethylsilyl)oxy-2,3-dimethylbutyl]-4-(tert-butyldiphenylsilyl)oxymethyl-1-(1-trimethylsilyloxybut-3-enyl)cyclohex-3-en-2-yl]-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-2-(2-propynyl)-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecane

英文别名

tert-butyl-[[(3S,4R)-4-[(2S,3R)-4-[tert-butyl(dimethyl)silyl]oxy-2,3-dimethylbutyl]-3-[(1S,2R,3R,5R,7S)-2-[tert-butyl(dimethyl)silyl]oxy-3-methyl-5-[[(4R,6R,8R,10S,13R)-13-methyl-10-prop-2-ynyl-13-triethylsilyloxy-5,7,9-trioxadispiro[5.1.58.26]pentadecan-4-yl]methyl]-6,8-dioxabicyclo[3.2.1]octan-7-yl]-4-(1-trimethylsilyloxybut-3-enyl)cyclohexen-1-yl]methoxy]-diphenylsilane

(2S,5R,6R,8R,10R)-10-[(1S,2R,3R,5R,7S)-2-(tert-butyldimethylsilyl)oxy-7-[(1R,2S)-1-[(2S,3R)-4-(tert-butyldimethylsilyl)oxy-2,3-dimethylbutyl]-4-(tert-butyldiphenylsilyl)oxymethyl-1-(1-trimethylsilyloxybut-3-enyl)cyclohex-3-en-2-yl]-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-2-(2-propynyl)-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecane化学式

CAS

1075244-26-6

化学式

C₇₈H₁₃₂O₁₀Si₅

mdl

——

分子量

1370.33

InChiKey

LJORAYJZCSTIKI-PODIDMSQSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

19.42
重原子数：

93
可旋转键数：

30
环数：

8.0
sp3杂化的碳原子比例：

0.77
拓扑面积：

92.3
氢给体数：

0
氢受体数：

10

反应信息

作为反应物：

描述：

(2S,5R,6R,8R,10R)-10-[(1S,2R,3R,5R,7S)-2-(tert-butyldimethylsilyl)oxy-7-[(1R,2S)-1-[(2S,3R)-4-(tert-butyldimethylsilyl)oxy-2,3-dimethylbutyl]-4-(tert-butyldiphenylsilyl)oxymethyl-1-(1-trimethylsilyloxybut-3-enyl)cyclohex-3-en-2-yl]-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-2-(2-propynyl)-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecane 在 [CpRu(MeCN)3]PF₆ 作用下，以丙酮为溶剂，反应 0.25h，以79%的产率得到(1R,3E,8S,11R,12R,15R,19R,21R,23R,24R,25S,26S,27S)-24-(tert-butyldimethylsilyl)oxy-1-[(2S,3R)-4-(tert-butyldimethylsilyl)oxy-2,3-dimethylbutyl]-29-(tert-butyldiphenylsilyl)oxymethyl-8,12:12,15:15,19:21,25:21,26-pentaepoxy-11,23-dimethyl-6-methylene-11-(triethylsilyl)oxy-2-(trimethylsilyl)oxybicyclo[25.4.0]hentriaconta-3,28-diene

参考文献：

名称：

品纳毒素A的全合成。

摘要：

DOI：

10.1002/anie.200802729
作为产物：

描述：

(1R,2S)-1-[1-[(2S,3R)-4-(tert-butyldimethylsilyl)oxy-2,3-dimethylbutyl]-2-[(1S,2R,3R,5R,7S)-2-(tert-butyldimethylsilyl)oxy-3-methyl-5-[(2S,5R,6R,8R,10R)-5-methyl-2-(2-propynyl)-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecan-10-ylmethyl]-6,8-dioxabicyclo[3.2.1]octan-7-yl]-4-(tert-butyldiphenylsilyl)oxymethyl-3-cyclohexene-1-yl]-3-buten-1-ol 、三甲基硅咪唑以四氢呋喃为溶剂，反应 48.0h，以98%的产率得到(2S,5R,6R,8R,10R)-10-[(1S,2R,3R,5R,7S)-2-(tert-butyldimethylsilyl)oxy-7-[(1R,2S)-1-[(2S,3R)-4-(tert-butyldimethylsilyl)oxy-2,3-dimethylbutyl]-4-(tert-butyldiphenylsilyl)oxymethyl-1-(1-trimethylsilyloxybut-3-enyl)cyclohex-3-en-2-yl]-3-methyl-6,8-dioxabicyclo[3.2.1]oct-5-ylmethyl]-5-methyl-2-(2-propynyl)-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecane

参考文献：

名称：

品纳毒素A的全合成。

摘要：

DOI：

10.1002/anie.200802729

点击查看最新优质反应信息

文献信息

Total Synthesis of Pinnatoxin A

作者：Seiichi Nakamura、Fumiaki Kikuchi、Shunichi Hashimoto

DOI：10.1002/anie.200802729

日期：2008.9.1

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分子结构分类

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反应信息

文献信息

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