[(E)-(1S,2S)-1-(Dimethoxy-phosphoryloxymethyl)-2-hydroxy-tetradec-3-enyl]-carbamic acid tert-butyl ester | 524730-25-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: [(E)-(1S,2S)-1-(Dimethoxy-phosphoryloxymethyl)-2-hydroxy-tetradec-3-enyl]-carbamic acid tert-butyl ester
• CAS: 524730-25-4
• 化学式: C₂₂H₄₄NO₇P
• 分子量: 465.568
• InChiKey: AHDOBRHEOHKGSK-KEENPFPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  31.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  103.32
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [(E)-(1S,2S)-1-(Dimethoxy-phosphoryloxymethyl)-2-hydroxy-tetradec-3-enyl]-carbamic acid tert-butyl ester 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Phosphoric acid mono-((E)-(2S,3S)-2-amino-3-hydroxy-pentadec-4-enyl) ester 、 (E)-(2R,3S)-2-Amino-1-bromo-pentadec-4-en-3-ol; hydrobromide
  参考文献：
  名称：

  Synthesis and biological properties of novel sphingosine derivatives

  摘要：

  Sphingosine-1-phosphate (S-1P) derivatives such as threo-(2S,3S)-analogues, which are C-3 stereoisomers of natural erythro-(2S,3R)-S-1P, have been synthesized starting from L-serine or (IS,2S)-2-amino-1-aryl-1,3-propanediols (6). threo-(IS,2R)2-Amino-1-aryl-3-bromopropanols (HBr salt) have also been prepared from 6. The threo-S-1Ps and the threo-amino-bromide derivatives have shown potent inhibitory activity against Ca2+ ion mobilization in HL60 cells induced by erythro-S-1P, suggesting that these compounds would compete with cell surface EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.010
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 在 吡啶 、 四溴化碳 、 溶剂黄146 、 zinc dibromide 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 [(E)-(1S,2S)-1-(Dimethoxy-phosphoryloxymethyl)-2-hydroxy-tetradec-3-enyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and biological properties of novel sphingosine derivatives

  摘要：

  Sphingosine-1-phosphate (S-1P) derivatives such as threo-(2S,3S)-analogues, which are C-3 stereoisomers of natural erythro-(2S,3R)-S-1P, have been synthesized starting from L-serine or (IS,2S)-2-amino-1-aryl-1,3-propanediols (6). threo-(IS,2R)2-Amino-1-aryl-3-bromopropanols (HBr salt) have also been prepared from 6. The threo-S-1Ps and the threo-amino-bromide derivatives have shown potent inhibitory activity against Ca2+ ion mobilization in HL60 cells induced by erythro-S-1P, suggesting that these compounds would compete with cell surface EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.010