2-[(E)-(S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-4,5-dimethyl-[1,3,2]dioxaborolane | 676609-77-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 2-[(E)-(S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-4,5-dimethyl-[1,3,2]dioxaborolane
• 英文别名: tert-butyl-[(E,2S)-2-[tert-butyl(dimethyl)silyl]oxy-4-(4,5-dimethyl-1,3,2-dioxaborolan-2-yl)but-3-enoxy]-dimethylsilane
• CAS: 676609-77-1
• 化学式: C₂₀H₄₃BO₄Si₂
• 分子量: 414.541
• InChiKey: RXHDRKWZJLAZFS-PLSAJLJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(E)-(S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-4,5-dimethyl-[1,3,2]dioxaborolane 、 [(1R,3S,5R,10S,13R,15R,16S,17S,19R,23S)-8,8-dimethyl-16-(naphthalen-2-ylmethoxy)-4,7,9,14,18,24-hexaoxapentacyclo[13.9.0.03,13.05,10.017,23]tetracosa-11,20-dien-19-yl] acetate 在 bis(triphenylphosphine)nickel(II) chloride 、 正丁基锂 、 sodium iodide 、 三甲基乙腈 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以22%的产率得到tert-butyl-[(E,2S)-2-[tert-butyl(dimethyl)silyl]oxy-4-[(1R,3S,5R,10S,13R,15R,16R,17S,21R,23S)-8,8-dimethyl-16-(naphthalen-2-ylmethoxy)-4,7,9,14,18,24-hexaoxapentacyclo[13.9.0.03,13.05,10.017,23]tetracosa-11,19-dien-21-yl]but-3-enoxy]-dimethylsilane
  参考文献：
  名称：

  Synthesis of the Fully Functionalized ABCDE Ring Moiety of Ciguatoxin

  摘要：

  A fully functionalized ABCDE ring moiety of ciguatoxin (CTX), the major causative agent of ciguatera poisoning, was synthesized for the first time. The present strategy involves the efficient installation of the C5-dihydroxybutenyl substituent and construction of the tetrahydrooxepin E ring using a novel alpha-chlorosulfide synthon.

  DOI：

  10.1021/ol0364475
• 作为产物：
  描述：

  (S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-yne 在 diisopinocampheylborane 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 2-[(E)-(S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-4,5-dimethyl-[1,3,2]dioxaborolane
  参考文献：
  名称：

  Synthesis of the Fully Functionalized ABCDE Ring Moiety of Ciguatoxin

  摘要：

  A fully functionalized ABCDE ring moiety of ciguatoxin (CTX), the major causative agent of ciguatera poisoning, was synthesized for the first time. The present strategy involves the efficient installation of the C5-dihydroxybutenyl substituent and construction of the tetrahydrooxepin E ring using a novel alpha-chlorosulfide synthon.

  DOI：

  10.1021/ol0364475

文献信息

• A very short route to the functionalized A-ring moiety of ciguatoxin
  作者：Hiroki Oguri、Shin-ichiro Tanaka、Tohru Oishi、Masahiro Hirama

  DOI：10.1016/s0040-4039(99)02185-1

  日期：2000.2

  The functionalized AB-ring moiety of ciguatoxin has been synthesized in a highly convergent manner via transition metal catalysis. (C) 2000 Elsevier Science Ltd. Alt rights reserved.
• Synthesis of the Fully Functionalized ABCDE Ring Moiety of Ciguatoxin
  作者：Shoji Kobayashi、Babak H. Alizadeh、Shin-ya Sasaki、Hiroki Oguri、Masahiro Hirama

  DOI：10.1021/ol0364475

  日期：2004.3.1

  A fully functionalized ABCDE ring moiety of ciguatoxin (CTX), the major causative agent of ciguatera poisoning, was synthesized for the first time. The present strategy involves the efficient installation of the C5-dihydroxybutenyl substituent and construction of the tetrahydrooxepin E ring using a novel alpha-chlorosulfide synthon.