(2R,3S,4aR,8S,9aS)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-8-ol | 934747-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4aR,8S,9aS)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-8-ol
• CAS: 934747-62-3
• 化学式: C₂₂H₄₆O₅Si₂
• 分子量: 446.775
• InChiKey: XKWQMZUGQTVPJB-LJDSDSDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4aR,8S,9aS)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-8-ol 在 咪唑 、 碘 、 四丁基碘化铵 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(2R,3S,4aR,8S,9aS)-3-[tert-butyl(dimethyl)silyl]oxy-8-(naphthalen-2-ylmethoxy)-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-2-yl]acetonitrile
  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：

  在 Grubbs catalyst first generation lithium aluminium tetrahydride 、 碳酸氢钠 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3S,4aR,8S,9aS)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,4,4a,6,7,8,9,9a-octahydro-2H-pyrano[3,2-b]oxepin-8-ol
  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

• Stereoselective synthesis of the left wing of Caribbean ciguatoxin
  作者：Shuji Yamashita、Ryohei Uematsu、Masahiro Hirama

  DOI：10.1016/j.tet.2011.05.080

  日期：2011.9

  Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are potent toxic polycyclic ethers. In this paper, we report a stereoselective and secure route to the left wing of Caribbean ciguatoxin on the basis of a 6-exo radical cyclization strategy. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.