tert-butyl [(3R,4R,5S)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl]carbamate | 1338778-27-0

• 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: tert-butyl [(3R,4R,5S)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl]carbamate
• CAS: 1338778-27-0
• 化学式: C₂₃H₄₅NO₄
• 分子量: 399.615
• InChiKey: GZEWDCOJEMICAG-QHAWAJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  28.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  67.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl [(3R,4R,5S)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2-epi-(-)-jaspine B
  参考文献：
  名称：

  Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C

  摘要：

  Sphingosine kinases (SphKs) are oncogenic enzymes that regulate the critical balance between ceramide and sphingosine-1-phosphate. Much effort has been dedicated to develop inhibitors against these enzymes. Naturally occurring pachastrissamine (jaspine B) and all its stereoisomers were prepared and evaluated for their inhibitory effects against SphKs. All eight stereoisomers exhibited moderate to potent inhibitory activity against SphK1 and SphK2. Inhibitory effects were profiled against protein kinase C (PKC) isoforms by in vitro experiments. Atypical PKCs (PKC zeta and PKC iota) were inhibited by several pachastrissamine stereoisomers. The improved activity over N,N-dimethylsphingosine suggests that the cyclic scaffold in pachastrissamines facilitates potential favorable interactions with SphKs and PKCs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.061
• 作为产物：
  描述：

  pentadecyltriphenylphosphonium bromide 在 4-二甲氨基吡啶 、 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三乙胺 、 对甲苯磺酰氯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 9.0h， 生成 tert-butyl [(3R,4R,5S)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl]carbamate
  参考文献：
  名称：

  Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C

  摘要：

  Sphingosine kinases (SphKs) are oncogenic enzymes that regulate the critical balance between ceramide and sphingosine-1-phosphate. Much effort has been dedicated to develop inhibitors against these enzymes. Naturally occurring pachastrissamine (jaspine B) and all its stereoisomers were prepared and evaluated for their inhibitory effects against SphKs. All eight stereoisomers exhibited moderate to potent inhibitory activity against SphK1 and SphK2. Inhibitory effects were profiled against protein kinase C (PKC) isoforms by in vitro experiments. Atypical PKCs (PKC zeta and PKC iota) were inhibited by several pachastrissamine stereoisomers. The improved activity over N,N-dimethylsphingosine suggests that the cyclic scaffold in pachastrissamines facilitates potential favorable interactions with SphKs and PKCs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.061

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。