tert-butyl (2S,3R)-3-(4-bromophenyl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate | 928653-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,3R)-3-(4-bromophenyl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S,3R)-3-(4-bromophenyl)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-oxopyrrolidine-1-carboxylate
• CAS: 928653-20-7
• 化学式: C₃₂H₃₈BrNO₄Si
• 分子量: 608.648
• InChiKey: NKGTVYIYNSCJKQ-VSGBNLITSA-N

物化性质

• 沸点：
  635.8±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.65
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R)-3-(4-bromophenyl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate 在 palladium on activated charcoal RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 二乙基异丙基胺 、 N-tritylprop-2-en-1-amine 、 氢气 、 四氯化钛 、 三乙基硼氢化锂 、 碳酸氢钠 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 乙酸乙酯 、 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：

  1,4-二溴苯 、 (2S)-2-[[[(叔丁基)二苯基硅]氧基]甲基]-2,5-二氢-5-氧代-1H-吡咯-1-羧酸叔丁酯 在 正丁基锂 、 copper(I) bromide dimethylsulfide complex 、 三甲基氯硅烷 作用下， 以 乙醚 为溶剂， 以94%的产率得到tert-butyl (2S,3R)-3-(4-bromophenyl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-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

文献信息

• In search of constrained FTY720 and phytosphingosine analogs as dual acting anticancer agents targeting metabolic and epigenetic pathways
  作者：Jean-Baptiste Garsi、Lorenzo Sernissi、Vito Vece、Stephen Hanessian、Alison N. McCracken、Grigor Simitian、Aimee L. Edinger

  DOI：10.1016/j.ejmech.2018.09.043

  日期：2018.11

  compounds containing pyrrolidine and pyrrolizidine cores with appended hydrophobic substituents were prepared as constrained analogs of FTY720 and phytosphingosine. The effect of these compounds on the viability of cancer cells, on downregulation of the nutrient transport systems, and on their ability to cause vacuolation was studied. An attempt to inhibit HDACs with some phosphate esters of our analogs

  制备了一系列含有吡咯烷和吡咯里西啶核心并附加疏水取代基的化合物作为 FTY720 和植物鞘氨醇的受限类似物。研究了这些化合物对癌细胞活力、营养转运系统下调及其引起空泡形成的能力的影响。我们尝试用我们类似物的一些磷酸酯抑制 HDAC，但由于我们未能重现报道的 FTY720-磷酸盐的抑制作用而受阻。