(S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde | 182072-78-2

• 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: (S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde
• 英文别名: (4S)-4-[tert-butyl(diphenyl)silyl]oxy-4-[(2S)-5-oxooxolan-2-yl]butanal
• CAS: 182072-78-2
• 化学式: C₂₄H₃₀O₄Si
• 分子量: 410.585
• InChiKey: RUFLGANPVVXCOS-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((E)-8-Benzyloxy-oct-4-enyl)-triphenyl-phosphonium; iodide 、 (S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde 在 sodium hexamethyldisilazane 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以68%的产率得到(S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one
  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-((R)-4-Benzyloxy-1-hydroxy-butyl)-dihydro-furan-2-one 在 palladium on activated charcoal 咪唑 、 盐酸 、 氢氧化钾 、 Celite 、 氢气 、 对甲苯磺酸 、 三苯基膦 、 pyridinium chlorochromate 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 二氯甲烷 、 丙酸 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 75.0h， 生成 (S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde
  参考文献：
  名称：

  走向丙酮酸乙酰化酶的化学文库。Trilobacin的全合成。

  摘要：

  DOI：

  10.1021/jo961286m

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.
• Toward Chemical Libraries of Annonaceous Acetogenins. Total Synthesis of Trilobacin
  作者：Subhash C. Sinha、Anjana Sinha、Ahmad Yazbak、Ehud Keinan

  DOI：10.1021/jo961286m

  日期：1996.1.1