(2R,3R,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran | 1108740-19-7

• 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: (2R,3R,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran
• 英文别名: tert-butyl ((3S,4R,5R)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl)carbamate；tert-butyl [(3S,4R,5R)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl]carbamate；tert-butyl N-[(3S,4R,5R)-4-hydroxy-5-tetradecyloxolan-3-yl]carbamate
• CAS: 1108740-19-7
• 化学式: C₂₃H₄₅NO₄
• 分子量: 399.615
• InChiKey: GZEWDCOJEMICAG-PWRODBHTSA-N

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：

  (2R,3R,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.25h， 生成 (2R,3R,4S)-4-amino-2-tetradecyltetrahydrofuran-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
• 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 34.0h， 生成 (2R,3R,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran
  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

• Synthesis of pachastrissamine (jaspine B) and its derivatives by the late-stage introduction of the C-2 alkyl side-chains using olefin cross metathesis
  作者：Yuji Yoshimitsu、Jun Miyagaki、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1016/j.tet.2013.03.091

  日期：2013.5

  An improved divergent synthesis of the four diastereomers of pachastrissamine from Garner's aldehyde has been reported. The common intermediate was synthesized by an indium-mediated acetoxyallylation reaction. The long alkyl side chain was introduced in the late stage of the synthesis using an olefin cross metathesis reaction. Biological evaluation of the chain modified analogs of the (2S,3S,4R)-isomer

  据报道，从加纳的醛中合成了四种帕斯帕司胺的非对映异构体的改进的发散性合成。常见的中间体是通过铟介导的乙酰氧基烯化反应合成的。在合成的后期，使用烯烃交叉复分解反应引入长烷基侧链。（2 S，3 S，4 R）-异构体的链修饰类似物的生物学评估表明，生物活性高度依赖于链长。
• Stereoselective Divergent Synthesis of Four Diastereomers of Pachastrissamine (Jaspine B)
  作者：Yuji Yoshimitsu、Shinsuke Inuki、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/jo1005284

  日期：2010.6.4

  A divergent short synthesis of four diastereomers of pachastrissamine was achieved. Natural pachastrissamine was synthesized through bis-tosylation of the common intermediate and cyclization. 2-epi-Pachastrissamine was obtained by monotosylation and spontaneous cyclization of D-ribo-phytosphingosine derivative. By use of regio- and stereospecific ring-opening reaction of the orthoester assisted by a Bee group as a key step, 3-epi- and 2,3-epi-pachastrissamines were synthesized. The three stereogenic centers of all the diastereomers were constructed by using Garner's aldehyde as the sole chiral source.
• 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.