ethyl 2-[(4aR,6S,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]acetate | 601495-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-[(4aR,6S,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]acetate
• CAS: 601495-18-5
• 化学式: C₂₃H₃₆O₆Si
• 分子量: 436.621
• InChiKey: NMNKDFPFQWXBSK-QBSQKGQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(4aR,6S,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]acetate 在 4 Angstroem MS N-甲基吗啉 、 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 samarium diiodide 、 pyridine-SO3 complex 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 (-)-diethyl tartrate 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 生成 (4aR,5aS,8R,9S,10aR,11aS)-8-Methyl-9-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-8-ol
  参考文献：
  名称：

  Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  [GRAPHICS]The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.

  DOI：

  10.1021/ol026804w
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 N-甲基吗啉 、 2,6-二甲基吡啶 、 盐酸 、 samarium diiodide 、 camphor-10-sulfonic acid 、 碳酸氢钠 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 生成 ethyl 2-[(4aR,6S,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]acetate
  参考文献：
  名称：

  Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  [GRAPHICS]The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.

  DOI：

  10.1021/ol026804w

文献信息

• Efficient strategy for convergent synthesis of trans-fused polycyclic ethers based on an intramolecular SmI2-promoted cyclization of iodo ester
  作者：Koji Kawamura、Hiroshi Hinou、Goh Matsuo、Tadashi Nakata

  DOI：10.1016/s0040-4039(03)01277-2

  日期：2003.7

  An efficient convergent strategy for the construction of a trans-fused 6-6-6-6-membered tetracyclic ether ring system was developed. The key steps involve coupling of two cyclic ethers by esterification, SmI2-promoted intramolecular reductive cyclization of iodo ester to hemiacetal, dehydration to dihydropyran, hydroboration, oxidation, intramolecular acetalization, and Lewis-acid catalyzed silane

  开发了一种有效的收敛策略，用于构建反式6-6-6-6元四环醚环系统。关键步骤包括通过酯化作用偶联两个环醚，将SmI 2促进的碘代酯分子内还原环化成半缩醛，脱水成二氢吡喃，氢硼化，氧化，分子内缩醛化和路易斯酸催化的硅烷还原。
• Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin
  作者：Keisuke Suzuki、Tadashi Nakata

  DOI：10.1021/ol026804w

  日期：2002.10.1

  [GRAPHICS]The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.