3,7,11,15,19,23,27-heptamethyloctaeicosa-2Z,6Z,10Z,14E,18E,22E,26-heptaen-1-ol | 81338-25-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,7,11,15,19,23,27-heptamethyloctaeicosa-2Z,6Z,10Z,14E,18E,22E,26-heptaen-1-ol
• 英文别名: heptaprenol wtttcccOH；(2Z,6Z,10Z,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-ol
• CAS: 81338-25-2
• 化学式: C₃₅H₅₈O
• 分子量: 494.845
• InChiKey: GXDCABNKZQORKZ-CVYOGTPCSA-N

物化性质

• 沸点：
  583.7±19.0 °C(Predicted)
• 密度：
  0.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  36.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,7,11,15,19,23,27-heptamethyloctaeicosa-2Z,6Z,10Z,14E,18E,22E,26-heptaen-1-ol 在 2,4,6-三甲基吡啶 、 甲基磺酰氯 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation

  摘要：

  Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E](3),[Z](7))-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl phosphate (Und-P). It was coupled with glycosyl phosphates to afford Und-PP-linked glycans, including core trisaccharide of Campylobacter jejuni N-glycan. Our synthetic method for Und-PP-linked glycan would provide various substrates as a useful tool for systematic analysis of bacterial protein N-glycosylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.032
• 作为产物：
  描述：

  3,7-dimethyl-10-oxo-2,6-decadienoate 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 lithium monoethoxyaluminum hydride 、 三氧化硫吡啶 、 草酸 、 lithium diisopropyl amide 作用下， 反应 7.5h， 生成 3,7,11,15,19,23,27-heptamethyloctaeicosa-2Z,6Z,10Z,14E,18E,22E,26-heptaen-1-ol
  参考文献：
  名称：

  Directed aldol condensation as a stereoselective method for the synthesis of Z-trisubstituted olefins

  摘要：

  DOI：

  10.1007/bf00948516

文献信息

• Novel approach to the stereoselective synthesis of polyprenols via directed aldol condensation. Preparation of heptaprenols ωtttcctOH.
  作者：N.Ya. Grigorieva、I.M. Avrutov、A.V. Semenovsky

  DOI：10.1016/s0040-4039(00)94132-7

  日期：1983.1
• Two approaches to stereospecific synthesis of polyprenols taking the synthesis of heptaprenol ?tttcccOH as an example
  作者：A. V. Semenovskii、N. Ya. Grigor'eva、I. M. Avrutov、V. V. Veselovskii、M. A. Novikova、A. M. Moiseenkov

  DOI：10.1007/bf00956241

  日期：1984.1
• GRIGOREVA, N. YA.;AVRUTOV, I. M.;PINSKER, O. A.;YUDINA, O. N.;LUTSENKO, A+, IZV. AN CCCP. CEP. XIM., 1985, N 8, 1824-1835
  作者：GRIGOREVA, N. YA.、AVRUTOV, I. M.、PINSKER, O. A.、YUDINA, O. N.、LUTSENKO, A+

  DOI：——

  日期：——
• Directed aldol condensation as a stereoselective method for the synthesis of Z-trisubstituted olefins
  作者：N. Ya. Grigor'eva、I. M. Avrutov、O. A. Pinsker、O. N. Yudina、A. I. Lutsenko、A. M. Moiseenkov

  DOI：10.1007/bf00948516

  日期：1985.8
• Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation
  作者：Yong Joo Lee、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1016/j.tet.2009.06.032

  日期：2009.8

  Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E](3),[Z](7))-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl phosphate (Und-P). It was coupled with glycosyl phosphates to afford Und-PP-linked glycans, including core trisaccharide of Campylobacter jejuni N-glycan. Our synthetic method for Und-PP-linked glycan would provide various substrates as a useful tool for systematic analysis of bacterial protein N-glycosylation. (C) 2009 Elsevier Ltd. All rights reserved.