(E)-(2S,3R,4R)-3-Methyl-9-trimethylsilanyl-non-6-en-8-yne-1,2,4-triol | 690634-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(2S,3R,4R)-3-Methyl-9-trimethylsilanyl-non-6-en-8-yne-1,2,4-triol
• CAS: 690634-44-7
• 化学式: C₁₃H₂₄O₃Si
• 分子量: 256.417
• InChiKey: MOOFXJKNFHRFRX-ZAGQHCIPSA-N

物化性质

• 沸点：
  391.4±42.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-(2S,3R,4R)-3-Methyl-9-trimethylsilanyl-non-6-en-8-yne-1,2,4-triol 在 sodium hydride 、 1-(2,4,6-三异丙基苯基磺酰)咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 以61%的产率得到(E)-(2R,3R)-2-(S)-Oxiranyl-8-trimethylsilanyl-oct-5-en-7-yn-3-ol
  参考文献：
  名称：

  Construction of a C(30−38) Dioxabicyclo[3.2.1]octane Subtarget for (+)-Sorangicin A, Exploiting a Regio- and Stereocontrolled Acid-Catalyzed Epoxide Ring Opening

  摘要：

  In this paper, we report assembly of the novel dioxabicyclo[3.2.1]octane subtarget (-)-2, comprising the signature structural element of the potent antibiotic (+)-sorangicin A (1). The synthesis was achieved in 15 steps (1.5% overall yield) via a series of acid-catalyzed epoxide ring openings, The first, facilitated by the complex of alkyne (+)-3 with Co-2(CO)(8), proceeded in a highly regio- and stereoselective fashion.

  DOI：

  10.1021/ol049644s
• 作为产物：
  描述：

  (2S,3R,4R)-1,2-Bis-(4-methoxy-benzyloxy)-3-methyl-9-trimethylsilanyl-nona-6,8-diyn-4-ol 在 lithium aluminium tetrahydride 、 ammonium cerium(IV) nitrate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 5.0h， 生成 (E)-(2S,3R,4R)-3-Methyl-9-trimethylsilanyl-non-6-en-8-yne-1,2,4-triol
  参考文献：
  名称：

  Construction of a C(30−38) Dioxabicyclo[3.2.1]octane Subtarget for (+)-Sorangicin A, Exploiting a Regio- and Stereocontrolled Acid-Catalyzed Epoxide Ring Opening

  摘要：

  In this paper, we report assembly of the novel dioxabicyclo[3.2.1]octane subtarget (-)-2, comprising the signature structural element of the potent antibiotic (+)-sorangicin A (1). The synthesis was achieved in 15 steps (1.5% overall yield) via a series of acid-catalyzed epoxide ring openings, The first, facilitated by the complex of alkyne (+)-3 with Co-2(CO)(8), proceeded in a highly regio- and stereoselective fashion.

  DOI：

  10.1021/ol049644s