(2S,3R,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran | 1108740-18-6

• 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,3R,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran
• 英文别名: tert-butyl ((3S,4R,5S)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl)carbamate；tert-butyl [(3S,4R,5S)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl]carbamate；tert-butyl-(3S,4R,5S)-4-hydroxy-5-tetradecyltetrahydrofuran-3-ylcarbamate；tert-butyl N-[(3S,4R,5S)-4-hydroxy-5-tetradecyloxolan-3-yl]carbamate
• CAS: 1108740-18-6
• 化学式: C₂₃H₄₅NO₄
• 分子量: 399.615
• InChiKey: GZEWDCOJEMICAG-PCCBWWKXSA-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：

  (2S,3R,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.25h， 生成 (2S,3R,4S)-4-amino-2-tetradecyltetrahydrofuran-3-ol hydrochloride
  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 32.0h， 生成 (2S,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

• A common approach to the total synthesis of l-arabino-, l-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from d-mannose
  作者：Miroslava Martinková、Kvetoslava Pomikalová、Jozef Gonda、Mária Vilková

  DOI：10.1016/j.tet.2013.07.028

  日期：2013.9

  for the total syntheses of the protected l-arabino- and l-ribo-C18-phytosphingosine (8 and 9, respectively), HCl salts of ent-2-epi-jaspine B (ent-6) and 3-epi-jaspine B (7) with efficient use of both flexible building blocks 26 and 27 was achieved. The key step of this approach was [3,3]-sigmatropic rearrangement of allylic trichloroacetimidate 21 and thiocyanate 22, which were derived from the known

  对于受保护的全合成的常用策略升-阿拉伯糖-和升-核糖-C 18 -phytosphingosine（8和9，分别地），盐酸的盐耳鼻喉科-2-外延-jaspine B（ENT - 6）和3-实现了有效利用柔性构件26和27的Epi- jaspine B（7）。该方法的关键步骤是烯丙基三氯乙酰亚胺酸酯21和硫氰酸酯22的[3,3]σ重排。，将其与已知的2,3衍生自：5,6-二- ö异亚丙基d -mannofuranose 18为手性的来源。利用维蒂希反应来安装侧链功能。
• 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.
• The formal synthesis of 3-epi jaspine B using stereoselective intramolecular oxa-Michael addition
  作者：G. Srinivas Rao、Neela Sudhakar、B. Venkateswara Rao、S. Jeelani Basha

  DOI：10.1016/j.tetasy.2010.07.018

  日期：2010.8

  The formal synthesis of 3-epi jaspine B was achieved by using a stereoselective intramolecular oxa-Michael addition. The diacetate derivative of 3-epi jaspine B was also synthesized. (C) 2010 Elsevier Ltd. All rights reserved.