(E)-(2S,3R,4R)-1,2-Bis-(4-methoxy-benzyloxy)-3-methyl-9-trimethylsilanyl-non-6-en-8-yn-4-ol | 690634-32-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(2S,3R,4R)-1,2-Bis-(4-methoxy-benzyloxy)-3-methyl-9-trimethylsilanyl-non-6-en-8-yn-4-ol
• 英文别名: (E,2S,3R,4R)-1,2-bis[(4-methoxyphenyl)methoxy]-3-methyl-9-trimethylsilylnon-6-en-8-yn-4-ol
• CAS: 690634-32-3
• 化学式: C₂₉H₄₀O₅Si
• 分子量: 496.719
• InChiKey: SJWYDGPXBKEHBE-FQEYIGKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(2S,3R,4R)-1,2-Bis-(4-methoxy-benzyloxy)-3-methyl-9-trimethylsilanyl-non-6-en-8-yn-4-ol 在 Oxone 、 ammonium cerium(IV) nitrate 、 chiral spiro compound 、 sodium hydride 、 potassium carbonate 、 1-(2,4,6-三异丙基苯基磺酰)咪唑 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 3.67h， 生成 (2R,3R)-3-(S)-Oxiranyl-1-((2R,3R)-3-trimethylsilanylethynyl-oxiranyl)-butan-2-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：

  2-[(4-甲氧基苯基)甲氧基]乙醛 在 potassium hexacyanoferrate(III) 四氧化锇 、 lithium aluminium tetrahydride 、 (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan) 、 sodium hydride 、 potassium carbonate 、 1-(2,4,6-三异丙基苯基磺酰)咪唑 作用下， 以 四氢呋喃 、 乙醚 、 水 、 叔丁醇 为溶剂， 反应 24.42h， 生成 (E)-(2S,3R,4R)-1,2-Bis-(4-methoxy-benzyloxy)-3-methyl-9-trimethylsilanyl-non-6-en-8-yn-4-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.