tert-butyl (2S,3R,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(4-octylphenyl)-5-prop-2-enylpyrrolidine-1-carboxylate | 928653-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (2S,3R,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(4-octylphenyl)-5-prop-2-enylpyrrolidine-1-carboxylate
• CAS: 928653-23-0
• 化学式: C₄₃H₆₁NO₃Si
• 分子量: 668.048
• InChiKey: QGTNYLIGAPXNDP-HOAOOSOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(4-octylphenyl)-5-prop-2-enylpyrrolidine-1-carboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 二乙基异丙基胺 、 N-tritylprop-2-en-1-amine 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 (2S,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Constrained azacyclic analogues of the immunomodulatory agent FTY720 as molecular probes for sphingosine 1-phosphate receptors

  摘要：

  Constrained azacyclic analogues of FTY720 were prepared starting with D- and L-pyroglutamic acids. One enantiomer was shown to be a substrate for sphingosine kinase 2, being phosphorylated 4-fold more efficiently than FTY720. Among the corresponding phosphates, two were found to have unusual specificity in binding to SIP receptors: while being inactive on SIPI and S1P3, they acted as potent agonists on S1P4 and S1P5. The phosphates may be useful to explore the biology and binding site of these receptors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.014
• 作为产物：
  描述：

  (2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-octyl-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 四氯化钛 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 tert-butyl (2S,3R,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(4-octylphenyl)-5-prop-2-enylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Constrained azacyclic analogues of the immunomodulatory agent FTY720 as molecular probes for sphingosine 1-phosphate receptors

  摘要：

  Constrained azacyclic analogues of FTY720 were prepared starting with D- and L-pyroglutamic acids. One enantiomer was shown to be a substrate for sphingosine kinase 2, being phosphorylated 4-fold more efficiently than FTY720. Among the corresponding phosphates, two were found to have unusual specificity in binding to SIP receptors: while being inactive on SIPI and S1P3, they acted as potent agonists on S1P4 and S1P5. The phosphates may be useful to explore the biology and binding site of these receptors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.014