(S)-3-((2R,8R,13R)-8,13-bis(tert-butyldimethylsilyloxy)-13-((2R,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-dodecyltetrahydro-2H-pyran-2-yl)-2-(tert-butyldiphenylsilyloxy)tridec-11-ynyl)-5-methylfuran-2(5H)-one | 1073516-03-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-((2R,8R,13R)-8,13-bis(tert-butyldimethylsilyloxy)-13-((2R,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-dodecyltetrahydro-2H-pyran-2-yl)-2-(tert-butyldiphenylsilyloxy)tridec-11-ynyl)-5-methylfuran-2(5H)-one
• 英文别名: (2S)-4-[(2R,8R,13R)-8,13-bis[[tert-butyl(dimethyl)silyl]oxy]-13-[(2R,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-dodecyloxan-2-yl]-2-[tert-butyl(diphenyl)silyl]oxytridec-11-ynyl]-2-methyl-2H-furan-5-one
• CAS: 1073516-03-6
• 化学式: C₆₉H₁₂₀O₇Si₄
• 分子量: 1174.05
• InChiKey: SBZDPNNGLYGRTH-XMGCSIGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.96
• 重原子数：
  80
• 可旋转键数：
  36
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-3-((2R,8R,13R)-8,13-bis(tert-butyldimethylsilyloxy)-13-((2R,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-dodecyltetrahydro-2H-pyran-2-yl)-2-(tert-butyldiphenylsilyloxy)tridec-11-ynyl)-5-methylfuran-2(5H)-one 在 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  A Concise and Modular Synthesis of Pyranicin

  摘要：

  A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.

  DOI：

  10.1021/ol802041c
• 作为产物：
  描述：

  (5S)-3-((S)-4-bromo-2-(tert-butyldiphenylsilyloxy)butyl)-5-methylfuran-2(5H)-one 、 在 potassium phosphate monohydrate 、 双(三环己基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以46 mg的产率得到(S)-3-((2R,8R,13R)-8,13-bis(tert-butyldimethylsilyloxy)-13-((2R,5R,6R)-5-(tert-butyldimethylsilyloxy)-6-dodecyltetrahydro-2H-pyran-2-yl)-2-(tert-butyldiphenylsilyloxy)tridec-11-ynyl)-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  A Concise and Modular Synthesis of Pyranicin

  摘要：

  A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.

  DOI：

  10.1021/ol802041c

文献信息

• A Concise and Modular Synthesis of Pyranicin
  作者：Nolan D. Griggs、Andrew J. Phillips

  DOI：10.1021/ol802041c

  日期：2008.11.6

  A modular, 13-step synthesis of the tetrahydropyran-containing annonaceous acetogenin pyranicin is reported. Key features are the use of an Achmatowicz oxidation-Kishi reduction sequence for the assembly of a pyranone from a furan and the application of Fu's alkyl-alkyl Suzuki coupling for subunit union.