methyl (E)-3-[(2R,3R)-3-[[(2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl]oxiran-2-yl]prop-2-enoate | 934747-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (E)-3-[(2R,3R)-3-[[(2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl]oxiran-2-yl]prop-2-enoate
• CAS: 934747-54-3
• 化学式: C₁₈H₂₂O₇
• 分子量: 350.368
• InChiKey: GHKRJSMAPBEKKF-HBLJAKINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[(2R,3R)-3-[[(2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl]oxiran-2-yl]prop-2-enoate 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到methyl (E)-3-[(2R,4aR,6S,7R,8aS)-7-hydroxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]prop-2-enoate
  参考文献：
  名称：

  Convergent synthesis of the ABCDE-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 convergent synthesis of the pentacyclic left half of C-CTX-1, based on a newly developed acyl radical strategy. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.102
• 作为产物：
  描述：

  (E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-en-1-ol 在 titanium(IV) isopropylate 叔丁基过氧化氢 、 pyridine-SO3 complex 、 4 Angstroem MS 、 四丁基氟化铵 、 二甲基亚砜 、 (-)-diethyl tartrate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl (E)-3-[(2R,3R)-3-[[(2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl]oxiran-2-yl]prop-2-enoate
  参考文献：
  名称：

  Convergent synthesis of the ABCDE-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 convergent synthesis of the pentacyclic left half of C-CTX-1, based on a newly developed acyl radical strategy. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.102

文献信息

• Convergent synthesis of the ABCDE-ring fragment of the Caribbean ciguatoxin C-CTX-1
  作者：Masayuki Inoue、Fumihito Saito、Masafumi Iwatsu、Yuuki Ishihara、Masahiro Hirama

  DOI：10.1016/j.tetlet.2007.01.102

  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 convergent synthesis of the pentacyclic left half of C-CTX-1, based on a newly developed acyl radical strategy. (c) 2007 Elsevier Ltd. All rights reserved.