jaspine B*TFA

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: jaspine B*TFA
• 英文别名: pachastrissamine trifluoroacetate；(2S,3S,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol trifluoroacetic acid；pachastrissamine*TFA；pachastrissamine trfluoroacetic acid salt；jaspine B trfluoroacetic acid salt；pachastrissamine TFA salt；jaspine B TFA salt；(2S,3S,4S)-4-amino-2-tetradecyloxolan-3-ol;2,2,2-trifluoroacetic acid
• 化学式: C₂HF₃O₂*C₁₈H₃₇NO₂
• 分子量: 413.521
• InChiKey: FRCJMCLHTWGJQM-UVJOBNTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  jaspine B*TFA 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 以97%的产率得到jaspine B
  参考文献：
  名称：

  Stereoselective total synthesis of Jaspine B (Pachastrissamine) utilizing iodocyclization and an investigation of its cytotoxic activity

  摘要：

  The stereoselective synthesis of Jaspine B has been achieved from easily available (S)-Garner's aldehyde. The trisubstituted tetrahydrofuran core of Jaspine B was constructed by utilizing a diastereoselective iodocyclization as the key step. Deiodination and debenzylation were performed in a single step by using n-Bu3SnH and ABCN as a conjugate catalyst system. The in vitro cytotoxicity of compounds 1 and la against 3 human cancer cell lines-A549 (lung), MCF7 (breast), and KB (oral): and a non-cancer cell line (NIH3T3) was determined by sulphorhodamine B based assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.003
• 作为产物：
  描述：

  1-N-tert-butyloxycarbonyl-3,4-O-isopropylidene-phytosphingosine 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 jaspine B*TFA
  参考文献：
  名称：

  A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine

  摘要：

  The highly stereoselective Grignard addition on chiralimine 8 and opening of chiral epoxide 9 with Grignard reagent have been used as key steps in the stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.170

文献信息

• The first synthesis of the anhydrophytosphingosine pachastrissamine (jaspine B) from Garner’s aldehyde
  作者：N. Sudhakar、A. Ravi Kumar、A. Prabhakar、B. Jagadeesh、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2004.11.035

  日期：2005.1

  The synthesis of the natural anhydrophytosphingosine pachastrissamine (jaspine B) 1a from Garner’s aldehyde is described.

  描述了由加纳的醛合成天然的脱水植物鞘氨醇pachastrissamine（茉莉花B）1a。
• Stereoselective synthesis of jaspine B from d-xylose
  作者：Jun Liu、Yuguo Du、Xiaomin Dong、Shucong Meng、Junjun Xiao、Lijian Cheng

  DOI：10.1016/j.carres.2006.08.011

  日期：2006.11

  The natural cytotoxic marine compound, jaspine B, is stereo selectively synthesized from D-Xylose in 11 linear steps with a 23.9% overall yield. The key step in the synthesis involves an iodine-induced debenzylation of a primary alcohol and the subsequent 2,5-cyclization to fit the required configuration of jaspine B. A preliminary bioassay shows strong inhibition activities against human MDA231, Hela, and CNE cell lines, indicating potential usage in various cancer treatments. (c) 2006 Elsevier Ltd. All rights reserved.
• A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine
  作者：G. Srinivas Rao、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2011.08.170

  日期：2011.11

  The highly stereoselective Grignard addition on chiralimine 8 and opening of chiral epoxide 9 with Grignard reagent have been used as key steps in the stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine. (C) 2011 Elsevier Ltd. All rights reserved.
• Stereoselective total synthesis of Jaspine B (Pachastrissamine) utilizing iodocyclization and an investigation of its cytotoxic activity
  作者：Partha Ghosal、Sama Ajay、Sanjeev Meena、Sudhir Sinha、Arun K. Shaw

  DOI：10.1016/j.tetasy.2013.07.003

  日期：2013.8

  The stereoselective synthesis of Jaspine B has been achieved from easily available (S)-Garner's aldehyde. The trisubstituted tetrahydrofuran core of Jaspine B was constructed by utilizing a diastereoselective iodocyclization as the key step. Deiodination and debenzylation were performed in a single step by using n-Bu3SnH and ABCN as a conjugate catalyst system. The in vitro cytotoxicity of compounds 1 and la against 3 human cancer cell lines-A549 (lung), MCF7 (breast), and KB (oral): and a non-cancer cell line (NIH3T3) was determined by sulphorhodamine B based assay. (C) 2013 Elsevier Ltd. All rights reserved.