(2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-octyl-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester | 928653-22-9

• 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: (2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-octyl-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,3R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(4-octylphenyl)-5-oxopyrrolidine-1-carboxylate
• CAS: 928653-22-9
• 化学式: C₄₀H₅₅NO₄Si
• 分子量: 641.966
• InChiKey: CZKVWXZGAWEAHR-LQFQNGICSA-N

物化性质

• 沸点：
  690.9±55.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.79
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-octyl-phenyl)-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 sodium tetrahydroborate 、 N-tritylprop-2-en-1-amine 、 四丁基氟化铵 、 四氯化钛 、 三乙基硼氢化锂 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 [(2R,4R,5S)-5-(hydroxymethyl)-4-(4-octylphenyl)pyrrolidin-2-yl]methanol;hydrochloride
  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：

  1,3,2-Benzodioxaborole, 2-(1E)-1-octenyl- 在 palladium on activated charcoal 四(三苯基膦)钯 、 氢气 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 乙酸乙酯 为溶剂， 生成 (2S,3R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-octyl-phenyl)-5-oxo-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

文献信息

• [EN] SYNTHETIC SPHINGOLIPID-LIKE MOLECULES, DRUGS, METHODS OF THEIR SYNTHESIS AND METHODS OF TREATMENT<br/>[FR] MOLÉCULES DE TYPE SPHINGOLIPIDE SYNTHÉTIQUES, MÉDICAMENTS, PROCÉDÉS POUR LEUR SYNTHÈSE ET PROCÉDÉS DE TRAITEMENT
  申请人：UNIV CALIFORNIA

  公开号：WO2017053990A1

  公开（公告）日：2017-03-30

  Small molecules comprised of azacyclic constrained sphingolipid-like compounds and methods of their synthesis are provided. Formulations and medicaments are also provided that are directed to the treatment of disease, such as, for example, neoplasms, cancers, and other diseases. Therapeutics are also provided containing a therapeutically effective dose of one or more small molecule compounds, present either as pharmaceutically effective salt or in pure form, including, but not limited to, formulations for oral, intravenous, or intramuscular administration.

  提供了由杂环约束的类鞘脂样化合物组成的小分子及其合成方法。还提供了用于治疗疾病的配方和药物，例如，肿瘤、癌症和其他疾病。还提供了含有一个或多个小分子化合物的治疗剂，其含有治疗有效剂量，可以作为药效盐或纯形式存在，包括但不限于口服、静脉注射或肌肉注射的配方。