(2S,3R,4E)-2-amino-1-(tert-butyldiphenylsilanyloxy)octadec-4-en-3-ol | 378756-01-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R,4E)-2-amino-1-(tert-butyldiphenylsilanyloxy)octadec-4-en-3-ol
• 英文别名: (E,2S,3R)-2-amino-1-[tert-butyl(diphenyl)silyl]oxyoctadec-4-en-3-ol
• CAS: 378756-01-5
• 化学式: C₃₄H₅₅NO₂Si
• 分子量: 537.902
• InChiKey: QZXQYPRJHXBKEW-OTODTCPZSA-N

物化性质

• 沸点：
  603.8±55.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  38
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-2-amino-1-(tert-butyldiphenylsilanyloxy)octadec-4-en-3-ol 、 硬脂酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以67%的产率得到N-[(E,2S,3R)-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxyoctadec-4-en-2-yl]octadecanamide
  参考文献：
  名称：

  Design and synthesis of caged ceramide: UV-responsive ceramide releasing system based on UV-induced amide bond cleavage followed by O–N acyl transfer

  摘要：

  Sphingolipids, recognized as membrane constructs and as key signaling molecules, have been studied to examine intracellular function. Some caged sphingolipids that release parent sphingolipids after exposure to UV-irradiation have been previously developed, but caged ceramide has yet to be reported. In this study, we report the design and synthesis of a caged ceramide. Photo-irradiation experiment clarified that the caged ceramide can be successfully converted to the parent ceramide by UV-irradiation. Introduction of an alkyne-handle moiety for further modification of the caged ceramide is also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.048
• 作为产物：
  描述：

  (4E)-1-(tert-butyldiphenylsilyloxy)-2-(N-tert-butyloxycarbonyl)aminooctadec-4-ene-3-ol 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以76%的产率得到(2S,3R,4E)-2-amino-1-(tert-butyldiphenylsilanyloxy)octadec-4-en-3-ol
  参考文献：
  名称：

  Design and synthesis of caged ceramide: UV-responsive ceramide releasing system based on UV-induced amide bond cleavage followed by O–N acyl transfer

  摘要：

  Sphingolipids, recognized as membrane constructs and as key signaling molecules, have been studied to examine intracellular function. Some caged sphingolipids that release parent sphingolipids after exposure to UV-irradiation have been previously developed, but caged ceramide has yet to be reported. In this study, we report the design and synthesis of a caged ceramide. Photo-irradiation experiment clarified that the caged ceramide can be successfully converted to the parent ceramide by UV-irradiation. Introduction of an alkyne-handle moiety for further modification of the caged ceramide is also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.048

文献信息

• Design and synthesis of caged ceramide: UV-responsive ceramide releasing system based on UV-induced amide bond cleavage followed by O–N acyl transfer
  作者：Akira Shigenaga、Hiroko Hirakawa、Jun Yamamoto、Keiji Ogura、Masaya Denda、Keiko Yamaguchi、Daisuke Tsuji、Kohji Itoh、Akira Otaka

  DOI：10.1016/j.tet.2011.04.048

  日期：2011.6

  Sphingolipids, recognized as membrane constructs and as key signaling molecules, have been studied to examine intracellular function. Some caged sphingolipids that release parent sphingolipids after exposure to UV-irradiation have been previously developed, but caged ceramide has yet to be reported. In this study, we report the design and synthesis of a caged ceramide. Photo-irradiation experiment clarified that the caged ceramide can be successfully converted to the parent ceramide by UV-irradiation. Introduction of an alkyne-handle moiety for further modification of the caged ceramide is also reported. (C) 2011 Elsevier Ltd. All rights reserved.