(2R,3R,4S,4aS,9aS)-2-Hydroxymethyl-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol | 917896-71-0

• 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,9aS)-2-Hydroxymethyl-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol
• 英文别名: (2R,3R,4S,4aS,9aS)-2-(hydroxymethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepin-3-ol
• CAS: 917896-71-0
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: PEOPRVJGLULKBE-ZPAWYTMASA-N

物化性质

• 沸点：
  575.9±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,4aS,9aS)-2-Hydroxymethyl-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到(2S,3S,4S,4aS,9aS)-2-Iodomethyl-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol
  参考文献：
  名称：

  Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using O,S-Acetals As Key Intermediates

  摘要：

  [GRAPHICS]Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.

  DOI：

  10.1021/ol062350h
• 作为产物：
  描述：

  (1S,3R,6R,8S,9R,10R)-6-(4-methoxyphenyl)-2,5,7,11-tetraoxatricyclo[8.5.0.03,8]pentadec-13-en-9-ol 在 四丁基碘化铵 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (2R,3R,4S,4aS,9aS)-2-Hydroxymethyl-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-ol
  参考文献：
  名称：

  Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using O,S-Acetals As Key Intermediates

  摘要：

  [GRAPHICS]Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.

  DOI：

  10.1021/ol062350h

文献信息

• Improved Synthesis of the A–E Ring Segment of Ciguatoxin CTX3C by Using Intramolecular Allylations
  作者：Tokihiro Tanaka、Hiroki Asakura、Rie Fujiwara、Kentaro Kumamoto、Hiroaki Izuka、Kengo Shiroma、Hiroyoshi Takamura、Isao Kadota

  DOI：10.1246/bcsj.20170390

  日期：2018.4.15

  An improved synthesis of the A–E ring segment of ciguatoxin CTX3C is described. The E ring segment was synthesized by the intramolecular reaction of allylic stannane and aldehyde with high stereoselectivity. Construction of the A–E ring framework was performed by using the intramolecular allylation of α-acetoxy ether followed by ring-closing metathesis.

  描述了雪卡毒素 CTX3C 的 A-E 环段的改进合成。E环段由烯丙基锡烷和醛的分子内反应合成，具有高立体选择性。A-E环骨架的构建是通过使用α-乙酰氧基醚的分子内烯丙基化然后闭环复分解来进行的。
• Convergent synthesis of the A–E ring segment of ciguatoxin CTX3C
  作者：Isao Kadota、Takashi Abe、Miyuki Uni、Hiroyoshi Takamura、Yoshinori Yamamoto

  DOI：10.1016/j.tet.2009.07.037

  日期：2009.9

  A convergent synthesis of the A–E ring segment of ciguatoxin CTX3C was achieved via the intramolecular allylation of an α-chloroacetoxy ether and subsequent ring-closing metathesis.

  通过α-氯乙酰氧基醚的分子内烯丙基化和随后的闭环易位，实现了瓜瓜毒素CTX3C A–E环段的融合合成。
• Synthesis of the A−F Fragment of the Pacific Ciguatoxin CTX3C by Iterative Ring‐Closing Metathesis and Tsuji–Trost Allylation
  作者：Myron Triantafyllakis、Sam Alexander、Sophie Woolford、Claire Wilson、J. Stephen Clark

  DOI：10.1002/chem.202303121

  日期：2023.12.22

  The fully functionalized A−F ring system of the Pacific ciguatoxin CTX3C suitable for coupling to the I−M fragment of the natural product, has been synthesized from a simple glucal derivative. A six-step sequence that features ring-closing metathesis and stereoselective palladium-mediated allylation has been deployed in an iterative manner to construct the medium-sized D and E rings.

  太平洋雪卡毒素 CTX3C 的全功能化 A−F 环系统适合与天然产物的 I−M 片段偶联，是由简单的葡萄糖衍生物合成的。以闭环复分解和立体选择性钯介导的烯丙基化为特征的六步序列已以迭代方式部署来构建中等大小的 D 和 E 环。
• Improved Synthesis of the A-E Ring Segment of Ciguatoxin CTX3C
  作者：Isao Kadota、Kengo Shiroma、Hiroki Asakura、Tokihiro Tanaka、Hiroyoshi Takamura

  DOI：10.3987/com-13-s(s)106

  日期：——

  The improved synthesis of the A-E ring segment of ciguatoxin CTX3C was performed via a highly convergent approach based on intramolecular allylation-RCM methodology.
• Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using <i>O</i>,<i>S</i>-Acetals As Key Intermediates
  作者：Masayuki Inoue、Shuji Yamashita、Yuuki Ishihara、Masahiro Hirama

  DOI：10.1021/ol062350h

  日期：2006.12.1

  [GRAPHICS]Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.