(2R,3R,4S,4aS,6S,7R,9aS)-6-[(E,3S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(4-methoxyphenyl)methoxy]but-1-enyl]-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-ol | 1037204-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,4aS,6S,7R,9aS)-6-[(E,3S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(4-methoxyphenyl)methoxy]but-1-enyl]-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-ol
• CAS: 1037204-50-4
• 化学式: C₅₉H₆₈O₉Si
• 分子量: 949.269
• InChiKey: YXCDUYXCWZNMLV-HMDCNOPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.78
• 重原子数：
  69
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-硝基苯基丝氰酸酯 、 (2R,3R,4S,4aS,6S,7R,9aS)-6-[(E,3S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(4-methoxyphenyl)methoxy]but-1-enyl]-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-ol 在 三丁基膦 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到[(E,2S)-4-[(2R,3R,4S,4aS,6R,9aS)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepin-6-yl]-2-[(4-methoxyphenyl)methoxy]but-3-enoxy]-tert-butyl-diphenylsilane
  参考文献：
  名称：

  A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin

  摘要：

  Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.145
• 作为产物：
  描述：

  (2S)-tert-butyl-[2-(4-methoxybenzyloxy)but-3-enyloxy]diphenylsilane 、 (2R,3R,4S,4aS,6S,7R,9aS)-6-ethenyl-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-ol 在 PCy₃RuCl₂(CHPh)diMesIm 作用下， 以 苯 为溶剂， 反应 6.5h， 以34%的产率得到(2R,3R,4S,4aS,6S,7R,9aS)-6-[(E,3S)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(4-methoxyphenyl)methoxy]but-1-enyl]-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-7-ol
  参考文献：
  名称：

  A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin

  摘要：

  Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.145

文献信息

• A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin
  作者：Isao Kadota、Takashi Abe、Miyuki Uni、Hiroyoshi Takamura、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2008.03.145

  日期：2008.5

  Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring. (C) 2008 Elsevier Ltd. All rights reserved.