(2R,3R,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol | 1108740-17-5

• 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-amino-2-tetradecyltetrahydrofuran-3-ol
• 英文别名: (2S,3R,4R)-4-amino-2-tetradecyltetrahydrofuran-3-ol；2,3-epi-jaspine B；(2R,3R,4S)-pachastrissamine；2,3-epi-pachastrissamine；C-2,C-3-epi-jaspine B；(2R,3R,4S)-4-amino-2-tetradecyloxolan-3-ol
• CAS: 1108740-17-5
• 化学式: C₁₈H₃₇NO₂
• 分子量: 299.497
• InChiKey: FBQCDJRSCUVUFL-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到(2R,3R,4S)-4-acetamido-2-tetradecyltetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  Stereoselective Synthesis and Biological Studies of the C2 and C3 Epimer and the Enantiomer of Pachastrissamine (Jaspine B)

  摘要：

  据报道，研究人员从 d-葡萄糖中合成了天麻素 B 的 C2 和 C3 外比体以及对映体。这些异构体以及雅司平 B 及其 C2 表亚体对 MCF7 细胞的细胞毒性与市售抗癌药物表柔比星相关。

  DOI：

  10.1055/s-0029-1217096
• 作为产物：
  描述：

  1-十四烯 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 sodium azide 、 palladium on activated carbon 、 氢气 、 溶剂黄146 、 三氟乙酸 、 methyloxirane 、 lithium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 61.34h， 生成 (2R,3R,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol
  参考文献：
  名称：

  Formation of tetrahydrofurans via a 5-endo-tet cyclization of aziridines – synthesis of (−)-pachastrissamine

  摘要：

  据报道，2-羟基烷基环氧乙烷或氮丙啶可以形成四氢呋喃。在温和条件下，氮丙啶的5-endo-tet环化/开环反应顺利进行，生成四氢呋喃（THFs）。相比之下，环氧乙烷的相应过程未能成功，需要通过一系列SN2取代/环化步骤才能形成THFs。本文描述了该过程在制备ent-(−)-pachastrissamine中的应用。

  DOI：

  10.1039/c3ob40797g

文献信息

• Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers viaη3-allylpalladium intermediates
  作者：Mikko Passiniemi、Ari M. P. Koskinen

  DOI：10.1039/c0ob00643b

  日期：——

  A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner's aldehyde. The furan framework is formed via an η3-allylpalladium intermediate.

  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。
• 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。
• Enantioselective Synthesis of Jaspine B (Pachastrissamine) and Its C-2 and/or C-3 Epimers
  作者：Josep Llaveria、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1002/ejoc.201001477

  日期：2011.3

  Jaspine B and its C-2 and/or C3 epimers have been enantio-selectively prepared from butadiene monoepoxide through a synthetic procedure consisting of allylic amination by palladium-catalyzed dynamic kinetic asymmetric transformation, cross metathesis, and stereoselective dihydroxylation as key steps.

  Jaspine B 及其 C-2 和/或 C3 差向异构体已经从丁二烯单环氧化物通过合成程序对映选择性制备，该合成程序包括通过钯催化的动态动力学不对称转化、交叉复分解和立体选择性二羟基化的烯丙基胺化作为关键步骤。
• 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.