(E)-(2R,3R)-2-(S)-Oxiranyl-8-trimethylsilanyl-oct-5-en-7-yn-3-ol | 690634-33-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(2R,3R)-2-(S)-Oxiranyl-8-trimethylsilanyl-oct-5-en-7-yn-3-ol
• 英文别名: (E,2R,3R)-2-[(2S)-oxiran-2-yl]-8-trimethylsilyloct-5-en-7-yn-3-ol
• CAS: 690634-33-4
• 化学式: C₁₃H₂₂O₂Si
• 分子量: 238.402
• InChiKey: NNVGXFRKUQPTKK-ZAGQHCIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-(2R,3R)-2-(S)-Oxiranyl-8-trimethylsilanyl-oct-5-en-7-yn-3-ol 在 Oxone 、 dicobalt octacarbonyl 、 chiral spiro compound 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.84h， 生成 (2R,3R,5R)-2-Ethynyl-5-((R)-(R)-1-oxiranyl-ethyl)-tetrahydro-furan-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,4S)-4,5-Bis-(4-methoxy-benzyloxy)-3-methyl-pentane-1,2-diol 在 lithium aluminium tetrahydride 、 ammonium cerium(IV) nitrate 、 sodium hydride 、 1-(2,4,6-三异丙基苯基磺酰)咪唑 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 12.59h， 生成 (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

文献信息

• 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
  作者：Amos B. Smith、Richard J. Fox

  DOI：10.1021/ol049644s

  日期：2004.4.1

  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.