methyl (E)-3-[(2R,3S,5R,6S)-5-(methoxymethoxy)-3,6-dimethyl-6-[(1S)-1-(naphthalen-2-ylmethoxy)but-3-enyl]-2-(3-oxopropyl)oxan-3-yl]oxybut-2-enoate | 934810-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (E)-3-[(2R,3S,5R,6S)-5-(methoxymethoxy)-3,6-dimethyl-6-[(1S)-1-(naphthalen-2-ylmethoxy)but-3-enyl]-2-(3-oxopropyl)oxan-3-yl]oxybut-2-enoate
• CAS: 934810-56-7
• 化学式: C₃₂H₄₂O₈
• 分子量: 554.681
• InChiKey: OGJSKNYOTBPZKY-UDWSECQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[(2R,3S,5R,6S)-5-(methoxymethoxy)-3,6-dimethyl-6-[(1S)-1-(naphthalen-2-ylmethoxy)but-3-enyl]-2-(3-oxopropyl)oxan-3-yl]oxybut-2-enoate 在 samarium diiodide 、 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 (2S,3R,4aS,6R,7S,9aR)-6-[(Z)-4-hydroxy-3-methoxybut-2-enyl]-3-(methoxymethoxy)-2,4a,6-trimethyl-2-[(1S)-1-(naphthalen-2-ylmethoxy)but-3-enyl]-3,4,7,8,9,9a-hexahydropyrano[3,2-b]oxepin-7-ol
  参考文献：
  名称：

  Synthesis of the LMN-ring fragment of the Caribbean ciguatoxin C-CTX-1

  摘要：

  Ciguatoxin C-CTX-1 was isolated as a principal causative toxin of ciguatera seafood poisoning in the Caribbean Sea, and is structurally classified as a ladder-shaped polycyclic ether. In this Letter, we report the synthesis of the tricyclic LMN-ring system of C-CTX-1. SmI2-mediated reductive cyclization efficiently constructed the seven-membered M-ring with the axially oriented 1,3-dimethyl structure. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.103
• 作为产物：
  描述：

  在 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 四丁基氟化铵 、 potassium tri-sec-butyl-borohydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 叔丁醇 为溶剂， 生成 methyl (E)-3-[(2R,3S,5R,6S)-5-(methoxymethoxy)-3,6-dimethyl-6-[(1S)-1-(naphthalen-2-ylmethoxy)but-3-enyl]-2-(3-oxopropyl)oxan-3-yl]oxybut-2-enoate
  参考文献：
  名称：

  Synthesis of the LMN-ring fragment of the Caribbean ciguatoxin C-CTX-1

  摘要：

  Ciguatoxin C-CTX-1 was isolated as a principal causative toxin of ciguatera seafood poisoning in the Caribbean Sea, and is structurally classified as a ladder-shaped polycyclic ether. In this Letter, we report the synthesis of the tricyclic LMN-ring system of C-CTX-1. SmI2-mediated reductive cyclization efficiently constructed the seven-membered M-ring with the axially oriented 1,3-dimethyl structure. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.103

文献信息

• Synthesis of the LMN-ring fragment of the Caribbean ciguatoxin C-CTX-1
  作者：Keita Yoshikawa、Masayuki Inoue、Masahiro Hirama

  DOI：10.1016/j.tetlet.2007.01.103

  日期：2007.3

  Ciguatoxin C-CTX-1 was isolated as a principal causative toxin of ciguatera seafood poisoning in the Caribbean Sea, and is structurally classified as a ladder-shaped polycyclic ether. In this Letter, we report the synthesis of the tricyclic LMN-ring system of C-CTX-1. SmI2-mediated reductive cyclization efficiently constructed the seven-membered M-ring with the axially oriented 1,3-dimethyl structure. (c) 2007 Elsevier Ltd. All rights reserved.