(2S,3S,4S)-4-azido-3-(benzyloxy)-2-((E,Z)-tetradec-1-enyl)tetrahydrofuran | 936946-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4S)-4-azido-3-(benzyloxy)-2-((E,Z)-tetradec-1-enyl)tetrahydrofuran
• CAS: 936946-81-5
• 化学式: C₂₅H₃₉N₃O₂
• 分子量: 413.604
• InChiKey: LIOGQGGBEUNJPB-SDHOMARFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  30.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  67.22
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-4-azido-3-(benzyloxy)-2-((E,Z)-tetradec-1-enyl)tetrahydrofuran 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 三氟乙酸 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 反应 5.0h， 以95%的产率得到jaspine B*TFA
  参考文献：
  名称：

  Stereoselective synthesis of jaspine B from d-xylose

  摘要：

  The natural cytotoxic marine compound, jaspine B, is stereo selectively synthesized from D-Xylose in 11 linear steps with a 23.9% overall yield. The key step in the synthesis involves an iodine-induced debenzylation of a primary alcohol and the subsequent 2,5-cyclization to fit the required configuration of jaspine B. A preliminary bioassay shows strong inhibition activities against human MDA231, Hela, and CNE cell lines, indicating potential usage in various cancer treatments. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.011
• 作为产物：
  描述：

  3,5-di-O-benzyl-D-xylofuranose 在 吡啶 、 sodium periodate 、 正丁基锂 、 sodium azide 、 碘 、 碳酸氢钠 、 氯化铵 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.26h， 生成 (2S,3S,4S)-4-azido-3-(benzyloxy)-2-((E,Z)-tetradec-1-enyl)tetrahydrofuran
  参考文献：
  名称：

  Stereoselective synthesis of jaspine B from d-xylose

  摘要：

  The natural cytotoxic marine compound, jaspine B, is stereo selectively synthesized from D-Xylose in 11 linear steps with a 23.9% overall yield. The key step in the synthesis involves an iodine-induced debenzylation of a primary alcohol and the subsequent 2,5-cyclization to fit the required configuration of jaspine B. A preliminary bioassay shows strong inhibition activities against human MDA231, Hela, and CNE cell lines, indicating potential usage in various cancer treatments. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.011

文献信息

• Stereoselective Synthesis of Cytotoxic Anhydrophytosphingosine Pachastrissamine (Jaspine B) from <scp>d</scp>-Xylose
  作者：Yuguo Du、Jun Liu、Robert J. Linhardt

  DOI：10.1021/jo051644y

  日期：2006.2.1

  The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC(50) = 0.01 microg/mL level, has been stereoselectively synthesized from D-xylose in 10 linear steps with 25.7% overall yield.
• An expedient route for the practical synthesis of pachastrissamine (jaspine B) starting from 3,4,6-tri-O-benzyl-d-galactal
  作者：L. Vijaya Raghava Reddy、P. Venkat Reddy、Arun K. Shaw

  DOI：10.1016/j.tetasy.2007.02.021

  日期：2007.3

  A practically efficient stereoselective synthesis of pachastrissamine (jaspine B) is described starting from 3,4,6-tri-O-benzyl-Dgalactal in eight steps and 11% overall yield. (c) 2007 Elsevier Ltd. All rights reserved.