tert-butyl-dimethyl-[[(1R,3R,6S,7R,9S,11R,13S,19S,20R)-20-(naphthalen-2-ylmethoxy)-7-prop-2-enyl-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-6-yl]oxy]silane | 776316-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl-dimethyl-[[(1R,3R,6S,7R,9S,11R,13S,19S,20R)-20-(naphthalen-2-ylmethoxy)-7-prop-2-enyl-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-6-yl]oxy]silane
• CAS: 776316-07-5
• 化学式: C₃₆H₄₈O₆Si
• 分子量: 604.859
• InChiKey: CCBLWCHUBKSLAD-ROGKRVQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl-dimethyl-[[(1R,3R,6S,7R,9S,11R,13S,19S,20R)-20-(naphthalen-2-ylmethoxy)-7-prop-2-enyl-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-6-yl]oxy]silane 在 盐酸 、 正丁基锂 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.25h， 生成
  参考文献：
  名称：

  Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

  摘要：

  The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.010
• 作为产物：
  描述：

  2-[(1R,3R,6S,7R,9S,11R,13S,19S,20R)-6-[tert-butyl(dimethyl)silyl]oxy-20-(naphthalen-2-ylmethoxy)-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-7-yl]acetonitrile 在 sodium hexamethyldisilazane 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 tert-butyl-dimethyl-[[(1R,3R,6S,7R,9S,11R,13S,19S,20R)-20-(naphthalen-2-ylmethoxy)-7-prop-2-enyl-2,8,12,18-tetraoxatetracyclo[9.9.0.03,9.013,19]icosa-4,15-dien-6-yl]oxy]silane
  参考文献：
  名称：

  Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

  摘要：

  The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.010

文献信息

• Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C
  作者：Shoji Kobayashi、Yusuke Takahashi、Kazuo Komano、Babak H. Alizadeh、Yuuya Kawada、Tohru Oishi、Shin-ichiro Tanaka、Yoshihiro Ogasawara、Shin-ya Sasaki、Masahiro Hirama

  DOI：10.1016/j.tet.2004.07.010

  日期：2004.9

  The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. (C) 2004 Elsevier Ltd. All rights reserved.