[(2R,3S)-3-(4-Benzyloxy-butyl)-oxiranyl]-methanol

• 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: [(2R,3S)-3-(4-Benzyloxy-butyl)-oxiranyl]-methanol
• 英文别名: [(2R,3S)-3-(4-phenylmethoxybutyl)oxiran-2-yl]methanol
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: WRNGITABMIYVKM-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-3-(4-Benzyloxy-butyl)-oxiranyl]-methanol 在 palladium dihydroxide 氢气 、 magnesium 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 54.5h， 生成 (9S,10S)-11-[tert-butyl(diphenyl)silyl]oxy-9-hydroxy-10-methylundec-1-en-5-one
  参考文献：
  名称：

  Access to Both Anomers of Pectenotoxin Spiroketals by Kinetic Spiroketalization

  摘要：

  A concise synthesis of both AB ring spiroisomers of the pectenotoxins is described. The nonanomeric AB spiroketal ring system of the pectenotoxins-1, -2, -3, and -6 is formed under very mild, kinetic spiroketalization conditions, along with the anomeric isomer. Only catalytic asymmetric transformations were used as the source of chirality in the synthesis route.

  DOI：

  10.1021/ol048321t
• 作为产物：
  描述：

  5-苄氧基-1-戊醇 在 草酰氯 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 [(2R,3S)-3-(4-Benzyloxy-butyl)-oxiranyl]-methanol
  参考文献：
  名称：

  Access to Both Anomers of Pectenotoxin Spiroketals by Kinetic Spiroketalization

  摘要：

  A concise synthesis of both AB ring spiroisomers of the pectenotoxins is described. The nonanomeric AB spiroketal ring system of the pectenotoxins-1, -2, -3, and -6 is formed under very mild, kinetic spiroketalization conditions, along with the anomeric isomer. Only catalytic asymmetric transformations were used as the source of chirality in the synthesis route.

  DOI：

  10.1021/ol048321t

文献信息

• Stereocontrolled total synthesis of lipoxins A
  作者：K. C. Nicolaou、C. A. Veale、S. E. Webber、H. Katerinopoulos

  DOI：10.1021/ja00311a048

  日期：1985.12

  Synthese de la lipoxine A (acide trihydroxy-5,6,15 eicosatetraene-7,9,11,13oique) et de ses isomeres tout-trans

  Synthese de la lipoxine A (acide trihydroxy-5,6,15 eicosatetraene-7,9,11,13oique) et de ses isomeres tout-trans
• Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation
  作者：Arun Kumar Perepogu、D. Raman、U.S.N. Murty、Vaidya Jayathirtha Rao

  DOI：10.1016/j.bioorg.2008.12.002

  日期：2009.4

  The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains. (C) 2008 Elsevier Inc. All rights reserved.
• Access to Both Anomers of Pectenotoxin Spiroketals by Kinetic Spiroketalization
  作者：Petri M. Pihko、Jatta E. Aho

  DOI：10.1021/ol048321t

  日期：2004.10.1

  A concise synthesis of both AB ring spiroisomers of the pectenotoxins is described. The nonanomeric AB spiroketal ring system of the pectenotoxins-1, -2, -3, and -6 is formed under very mild, kinetic spiroketalization conditions, along with the anomeric isomer. Only catalytic asymmetric transformations were used as the source of chirality in the synthesis route.