(2S,3S,4S)-4-(tert-butyloxycarbonylamino)-2-(tetradecyl)tetrahydrofuran-3-ol | 838864-68-9

• 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: (2S,3S,4S)-4-(tert-butyloxycarbonylamino)-2-(tetradecyl)tetrahydrofuran-3-ol
• 英文别名: tert-butyl (3S,4S,5S)-4-hydroxy-5-tetradecyltetrahydrofuran-3-ylcarbamate；(2S,3S,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran；tert-butyl N-[(3S,4S,5S)-4-hydroxy-5-tetradecyloxolan-3-yl]carbamate
• CAS: 838864-68-9
• 化学式: C₂₃H₄₅NO₄
• 分子量: 399.615
• InChiKey: GZEWDCOJEMICAG-ACRUOGEOSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  519.8±50.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-4-(tert-butyloxycarbonylamino)-2-(tetradecyl)tetrahydrofuran-3-ol 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 (2S,3S,4S)-4-acetamido-2-tetradecyltetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  车菊酯胺（茉莉B）的立体选择性合成

  摘要：

  描述了对映体纯形式的天然脱水植物鞘氨醇pachastrissamine（jaspine B），一种从海绵中分离出来的代谢物的立体选择性合成。手性环氧化物（R）-缩水甘油是起始原料。该合成的关键步骤是无尖锐的不对称环氧化，由三氯乙酰亚胺酸酯基团介导的分子内立体特异性环氧化物开环和通过分子内亲核取代形成四氢呋喃环。

  DOI：

  10.1016/j.tet.2006.03.073
• 作为产物：
  描述：

  1-十四烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 45.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 (2S,3S,4S)-4-(tert-butyloxycarbonylamino)-2-(tetradecyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Pachastrissamine（Jaspine B）及其非对映体的不对称合成经由η 3 π-烯丙基中间体

  摘要：

  合成以下物质的捷径 Pachastrissamine （茉莉花B），脱水鞘氨醇衍生物及其所有三个非对映异构体。该路线仅由市售Garner醛中的9个步骤组成。呋喃框架形成经由一个η 3 π-烯丙基中间体。

  DOI：

  10.1039/c0ob00643b

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 total synthesis of pachastrissamine (jaspine B)
  作者：Mikko Passiniemi、Ari M.P. Koskinen

  DOI：10.1016/j.tetlet.2007.12.014

  日期：2008.2

  A short total synthesis of the cytotoxic natural product pachastrissamine is described. The synthesis includes eight steps starting from Garner's aldehyde and proceeds in 20% overall yield. Pd(0)-mediated intramolecular cyclisation and Ru-mediated cross-metathesis are the key reactions in this sequence. (c) 2007 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.
• Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines
  作者：Daniel Canals、David Mormeneo、Gemma Fabriàs、Amadeu Llebaria、Josefina Casas、Antonio Delgado

  DOI：10.1016/j.bmc.2008.11.026

  日期：2009.1

  The synthesis of isomeric jaspines (anhydro phytosphingosines), arising from intramolecular cyclization of the corresponding phytosphingosines with different con. gurations at C3 and C4 positions of the sphingoid backbone, is reported. Natural jaspine B is the most cytotoxic isomer on A549 cells and it induces cell death in a dose-dependent manner. The cytotoxicity of jaspine B has been correlated with a significant increase of intracellular dihydroceramides, which seem to play an active role in autophagy. (c) 2008 Elsevier Ltd. All rights reserved.