(4R)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5S)-5-[(2S,5S)-5-[(2R)-5-oxooxolan-2-yl]oxolan-2-yl]oxolan-2-yl]butanal | 862557-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5S)-5-[(2S,5S)-5-[(2R)-5-oxooxolan-2-yl]oxolan-2-yl]oxolan-2-yl]butanal
• CAS: 862557-91-3
• 化学式: C₂₂H₃₈O₆Si
• 分子量: 426.626
• InChiKey: SMXAZNRJXOGBIX-IPJCAIGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5S)-5-[(2S,5S)-5-[(2R)-5-oxooxolan-2-yl]oxolan-2-yl]oxolan-2-yl]butanal 在 palladium on activated charcoal 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 1.16h， 生成 (4R,5S,8S,9S,12R,13R)-5:8,9:12-dioxido-13-tert-butyldimethylsilyloxy-tricosan-1,4-olide
  参考文献：
  名称：

  A Bidirectional Approach to the Synthesis of a Complete Library of Adjacent-Bis-THF Annonaceous Acetogenins

  摘要：

  Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.

  DOI：

  10.1021/jo050697c
• 作为产物：
  描述：

  (R)-5-((4E,8E)-(S)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one 在 palladium on activated charcoal 、 四丙基高钌酸铵 N-甲基吲哚酮 、 lutidine 、 氢气 、 rhenium(VII) oxide 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.75h， 生成 (4R)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5S)-5-[(2S,5S)-5-[(2R)-5-oxooxolan-2-yl]oxolan-2-yl]oxolan-2-yl]butanal
  参考文献：
  名称：

  A Bidirectional Approach to the Synthesis of a Complete Library of Adjacent-Bis-THF Annonaceous Acetogenins

  摘要：

  Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.

  DOI：

  10.1021/jo050697c

文献信息

• A Bidirectional Approach to the Synthesis of a Complete Library of Adjacent-Bis-THF Annonaceous Acetogenins
  作者：Sanjib Das、Lian-Sheng Li、Sunny Abraham、Zhiyong Chen、Subhash C. Sinha

  DOI：10.1021/jo050697c

  日期：2005.7.1

  Thirty-six stereoisomers of bifunctional adjacent bis-THF (tetrahydrofuran) lactones have been synthesized, which can afford a complete library of the adjacent bis-THF Annonaceous acetogenins. The bis-THF lactones were synthesized, starting from the enantioselectively pure 8,9:12,13-(E,E and Z,E)-16-benzyloxy-5-hydroxy-hexadeca-1,4-olide, in a highly distereoselective manner using oxidative reactions, including rhenium(VII) oxides-mediated oxidative cyclization, Shi's asymmetric epoxidation, and Sharpless asymmetric dihydroxylation reactions. Using the nonsymmetrical bis-THF lactones, syntheses of two nonnatural acetogenins were achieved.