| 615284-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• CAS: 615284-65-6
• 化学式: C₄₇H₇₆O₉S₂Si
• 分子量: 877.333
• InChiKey: HAUKQICMISHBDT-SWXTWPJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.85
• 重原子数：
  59
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  在 tris-(dibenzylideneacetone)dipalladium(0) 吡啶 、 2,6-二甲基吡啶 、 三乙基硼 、 三苯胂 、 四丁基氟化铵 、 三正丁基氢锡 、 二异丁基氢化铝 、 potassium carbonate 、 氟化氢吡啶 、 N,N-二异丙基乙胺 、 [双(三氟乙酰氧基)碘]苯 、 lithium chloride 作用下， 以 四氢呋喃 、 吡啶 、 N-甲基吡咯烷酮 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 58.25h， 生成
  参考文献：
  名称：

  拟议的azaspiracid-1结构的全合成，第2部分：C1-C20，C21-C27和C28-C40片段的偶联和合成完成。

  摘要：

  DOI：

  10.1002/anie.200351826
• 作为产物：
  描述：

  (2R,3aS,5R,5'R,6S,6''S,7aS)-6-methyl-6''-((E)-5-(pivaloyloxy)pent-1-en-1-yl)-2,3,3a,3',4',5'',6,6'',7,7a-decahydrodispiro[furo[3,2-b]pyran-5,2'-furan-5',2''-pyran]-2-carboxylic acid 在 正丁基锂 、 二丁基镁 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.25h， 生成
  参考文献：
  名称：

  Total Synthesis and Structural Elucidation of Azaspiracid-1. Synthesis-Based Analysis of Originally Proposed Structures and Indication of Their Non-Identity to the Natural Product

  摘要：

  The key building blocks (6, 7, and 8) for the intended construction of the originally proposed structures of azaspiracid-1, a potent marine-derived neurotoxin, were coupled and the products elaborated to the targeted compounds (1a,b) and their C-20 epimers (2 and 3). The assembly of the three intermediates was accomplished by a dithiane-based coupling reaction that united the C-1 - C-20 (7) and C-21 - C-27 (8) fragments, followed by a Stille-type coupling which allowed the incorporation of the C-28 - C-40 fragment (6) into the growing substrate. Neither of the final products (1a,b) matched the natural substance by TLC or H-1 NMR spectroscopic analysis, suggesting one or more errors in the originally proposed structure for this notorious biotoxin.

  DOI：

  10.1021/ja054748z

文献信息

• Total Synthesis of the Proposed Azaspiracid-1 Structure, Part 2: Coupling of the C1–C20, C21–C27, and C28–C40 Fragments and Completion of the Synthesis
  作者：K. C. Nicolaou、David Y.-K. Chen、Yiwei Li、Wenyuan Qian、Taotao Ling、Stepan Vyskocil、Theocharis V. Koftis、Mugesh Govindasamy、Noriaki Uesaka

  DOI：10.1002/anie.200351826

  日期：2003.8.11
• Total Synthesis and Structural Elucidation of Azaspiracid-1. Synthesis-Based Analysis of Originally Proposed Structures and Indication of Their Non-Identity to the Natural Product
  作者：K. C. Nicolaou、David Y.-K. Chen、Yiwei Li、Noriaki Uesaka、Goran Petrovic、Theocharis V. Koftis、Federico Bernal、Michael O. Frederick、Mugesh Govindasamy、Taotao Ling、Petri M. Pihko、Wenjun Tang、Stepan Vyskocil

  DOI：10.1021/ja054748z

  日期：2006.2.1

  The key building blocks (6, 7, and 8) for the intended construction of the originally proposed structures of azaspiracid-1, a potent marine-derived neurotoxin, were coupled and the products elaborated to the targeted compounds (1a,b) and their C-20 epimers (2 and 3). The assembly of the three intermediates was accomplished by a dithiane-based coupling reaction that united the C-1 - C-20 (7) and C-21 - C-27 (8) fragments, followed by a Stille-type coupling which allowed the incorporation of the C-28 - C-40 fragment (6) into the growing substrate. Neither of the final products (1a,b) matched the natural substance by TLC or H-1 NMR spectroscopic analysis, suggesting one or more errors in the originally proposed structure for this notorious biotoxin.