1,4-anhydro-(2S,3S,4R)-2-N-tert-butoxycarbonylamino-1,3,4-octadecanetriol | 838864-70-3

• 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: 1,4-anhydro-(2S,3S,4R)-2-N-tert-butoxycarbonylamino-1,3,4-octadecanetriol
• 英文别名: N-tert-butoxycarbonyl-4-epi-pachastrissamine；(2R,3S,4S)-4-(tert-butoxycarbonyl)amino-3-hydroxy-2-tetradecyltetrahydrofuran；tert-butyl ((3S,4S,5R)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl)carbamate；tert-butyl N-[(3S,4S,5R)-4-hydroxy-5-tetradecyloxolan-3-yl]carbamate
• CAS: 838864-70-3
• 化学式: C₂₃H₄₅NO₄
• 分子量: 399.615
• InChiKey: GZEWDCOJEMICAG-HBMCJLEFSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  519.8±50.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

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：

  1,4-anhydro-(2S,3S,4R)-2-N-tert-butoxycarbonylamino-1,3,4-octadecanetriol 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,3S,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 28.0h， 生成 1,4-anhydro-(2S,3S,4R)-2-N-tert-butoxycarbonylamino-1,3,4-octadecanetriol
  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。
• The first synthesis of the anhydrophytosphingosine pachastrissamine (jaspine B) from Garner’s aldehyde
  作者：N. Sudhakar、A. Ravi Kumar、A. Prabhakar、B. Jagadeesh、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2004.11.035

  日期：2005.1

  The synthesis of the natural anhydrophytosphingosine pachastrissamine (jaspine B) 1a from Garner’s aldehyde is described.

  描述了由加纳的醛合成天然的脱水植物鞘氨醇pachastrissamine（茉莉花B）1a。
• A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl d-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B
  作者：G. Srinivas Rao、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2011.07.032

  日期：2011.9

  A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl D-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B was achieved by using Grignard addition on N-benzyl sugar lactamine and Wittig olefination as key steps. (C) 2011 Elsevier Ltd. All rights reserved.
• An Efficient Synthesis of the Natural Tetrahydrofuran Pachastrissamine Starting from <scp>d</scp>-<i>ribo</i>-Phytosphingosine
  作者：Richard J. B. H. N. van den Berg、Thomas J. Boltje、Carlo P. Verhagen、Remy E. J. N. Litjens、Gijsbert A. van der Marel、Herman S. Overkleeft

  DOI：10.1021/jo0520240

  日期：2006.1.1

  [GRAPHICS]The natural product pachastrissamine, an anhydrophytosphingosine derivative isolated from various sponges and endowed with cytotoxic activity against several human carcinoma cell lines, was synthesized in three steps and with 72% overall yield from D-ribo-phytosphingosine.
• 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.