Cer(t18:1(6OH)/16:0(2OH))

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Cer(t18:1(6OH)/16:0(2OH))
• 英文别名: 2-hydroxy-N-[(E,2S,3R,6R)-1,3,6-trihydroxyoctadec-4-en-2-yl]hexadecanamide
• 化学式: C₃₄H₆₇NO₅
• 分子量: 569.91
• InChiKey: FDCYWFADVRIZMH-GXRVLAEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40.0
• 可旋转键数：
  30.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  110.02
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  methyl (R)-2-hydroxyhexadecanoate 在 吡啶 、 lithium hydroxide monohydrate 、 potassium carbonate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 62.0h， 生成 Cer(t18:1(6OH)/16:0(2OH))
  参考文献：
  名称：

  Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy

  摘要：

  In this paper, a new synthetic route toward 6-hydroxysphingosine and alpha-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.

  DOI：

  10.1021/acs.joc.5b00823

文献信息

• Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy
  作者：Patrick Wisse、Mark A. R. de Geus、Gen Cross、Adrianus M. C. H. van den Nieuwendijk、Eva J. van Rooden、Richard J. B. H. N. van den Berg、Johannes M. F. G. Aerts、Gijsbert A. van der Marel、Jeroen D. C. Codée、Herman S. Overkleeft

  DOI：10.1021/acs.joc.5b00823

  日期：2015.7.17

  In this paper, a new synthetic route toward 6-hydroxysphingosine and alpha-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.