tert-butyl [(2R,3R,4S)-3,4-dihydroxy-1-(triisopropylsilyloxy)octadecan-2-yl]carbamate | 1338778-28-1

• 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: tert-butyl [(2R,3R,4S)-3,4-dihydroxy-1-(triisopropylsilyloxy)octadecan-2-yl]carbamate
• CAS: 1338778-28-1
• 化学式: C₃₂H₆₇NO₅Si
• 分子量: 573.973
• InChiKey: XADHILSWGYGALT-DYIKCSJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.88
• 重原子数：
  39.0
• 可旋转键数：
  22.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  88.02
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl [(2R,3R,4S)-3,4-dihydroxy-1-(triisopropylsilyloxy)octadecan-2-yl]carbamate 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 四丁基氟化铵 、 三甲胺盐酸盐 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 tert-butyl ((3R,4S,5S)-4-hydroxy-5-tetradecyltetrahydrofuran-3-yl)carbamate
  参考文献：
  名称：

  Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C

  摘要：

  Sphingosine kinases (SphKs) are oncogenic enzymes that regulate the critical balance between ceramide and sphingosine-1-phosphate. Much effort has been dedicated to develop inhibitors against these enzymes. Naturally occurring pachastrissamine (jaspine B) and all its stereoisomers were prepared and evaluated for their inhibitory effects against SphKs. All eight stereoisomers exhibited moderate to potent inhibitory activity against SphK1 and SphK2. Inhibitory effects were profiled against protein kinase C (PKC) isoforms by in vitro experiments. Atypical PKCs (PKC zeta and PKC iota) were inhibited by several pachastrissamine stereoisomers. The improved activity over N,N-dimethylsphingosine suggests that the cyclic scaffold in pachastrissamines facilitates potential favorable interactions with SphKs and PKCs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.061
• 作为产物：
  描述：

  tert-butyl (S,Z)-2,2-dimethyl-4-(hexadec-1'-en-1'-yl)oxazolidine-3-carboxylate 在 咪唑 、 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 9.0h， 生成 tert-butyl [(2R,3R,4S)-3,4-dihydroxy-1-(triisopropylsilyloxy)octadecan-2-yl]carbamate
  参考文献：
  名称：

  Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C

  摘要：

  Sphingosine kinases (SphKs) are oncogenic enzymes that regulate the critical balance between ceramide and sphingosine-1-phosphate. Much effort has been dedicated to develop inhibitors against these enzymes. Naturally occurring pachastrissamine (jaspine B) and all its stereoisomers were prepared and evaluated for their inhibitory effects against SphKs. All eight stereoisomers exhibited moderate to potent inhibitory activity against SphK1 and SphK2. Inhibitory effects were profiled against protein kinase C (PKC) isoforms by in vitro experiments. Atypical PKCs (PKC zeta and PKC iota) were inhibited by several pachastrissamine stereoisomers. The improved activity over N,N-dimethylsphingosine suggests that the cyclic scaffold in pachastrissamines facilitates potential favorable interactions with SphKs and PKCs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.061