(R)-tert-butyl 4-(hexadec-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate | 528852-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-tert-butyl 4-(hexadec-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4R)-4-hexadec-1-enyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 528852-37-1
• 化学式: C₂₆H₄₉NO₃
• 分子量: 423.68
• InChiKey: FYNWNVPSPLZBPW-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (R)-tert-butyl 4-(hexadec-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以96%的产率得到(R)-4-Hexadecyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate stereoisomers and analogues and Their interaction with EDG receptors

  摘要：

  Sphingosine-1-phosphate (S1P) is considered to be an important regulator of diverse biological processes acting as a natural ligand to EDG receptors. As a preliminary study to develop potent and selective agonist and antagonist for EDG receptors, we report synthesis of S1P stereoisomers and analogues and their binding affinities to EDG-1, -3, and -5. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00893-4
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 、 pentadecyltriphenylphosphonium bromide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(R)-tert-butyl 4-(hexadec-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate stereoisomers and analogues and Their interaction with EDG receptors

  摘要：

  Sphingosine-1-phosphate (S1P) is considered to be an important regulator of diverse biological processes acting as a natural ligand to EDG receptors. As a preliminary study to develop potent and selective agonist and antagonist for EDG receptors, we report synthesis of S1P stereoisomers and analogues and their binding affinities to EDG-1, -3, and -5. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00893-4

文献信息

• Protein and peptide-free synthetic vaccines against streptococcus pneumoniae type 3
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2851092A1

  公开（公告）日：2015-03-25

  The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

  本发明提供了一种不含蛋白质和多肽的缀合物，该缀合物包括一种合成碳水化合物和一个载体分子，其中合成碳水化合物是与肺炎链球菌3型荚膜多糖相关的碳水化合物，载体分子是一种糖鞘脂。所述缀合物及其药物组合物可用于免疫预防与肺炎链球菌相关的疾病，特别是与肺炎链球菌3型相关的疾病。
• CARBOHYDRATE-GLYCOLIPID CONJUGATE VACCINES
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：US20150238597A1

  公开（公告）日：2015-08-27

  The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.

  本发明涉及合成和生物评价一种新型基于碳水化合物的疫苗的领域。这种新疫苗由多模块结构组成，可以将疫苗应用于各种病原体。该方法允许制备针对所有表达免疫原碳水化合物抗原的病原体的疫苗。由于不需要将抗原碳水化合物与蛋白质结合，所以结合疫苗尤其耐热稳定。无需冷藏，这是基于蛋白质的疫苗的一个主要缺点。
• Protein and peptide-free synthetic vaccines against Streptococcus pneumoniae type 3
  申请人：MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFTEN E.V.

  公开号：US10052373B2

  公开（公告）日：2018-08-21

  The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

  本发明提供了一种不含蛋白质和肽的共轭物，该共轭物由合成碳水化合物和载体分子组成，其中合成碳水化合物为肺炎链球菌3型荚膜多糖相关碳水化合物，载体分子为糖磷脂。所述共轭物及其药物组合物可用于肺炎链球菌相关疾病的免疫接种，更具体地说，可用于肺炎链球菌3型相关疾病的免疫接种。
• Carbohydrate-glycolipid conjugate vaccines
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：US10588962B2

  公开（公告）日：2020-03-17

  The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.

  本发明涉及一类基于碳水化合物的新型疫苗的合成和生物评估领域。这种新型疫苗由多模块结构组成，可将疫苗应用于各种病原体。这种方法可以制备出针对所有表达免疫原性碳水化合物抗原的病原体的疫苗。由于不需要将抗原碳水化合物与蛋白质共轭，共轭疫苗的热稳定性特别好。无需冷藏，这是基于蛋白质的疫苗的一个主要缺点。
• Stereoselective Divergent Synthesis of Four Diastereomers of Pachastrissamine (Jaspine B)
  作者：Yuji Yoshimitsu、Shinsuke Inuki、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/jo1005284

  日期：2010.6.4

  A divergent short synthesis of four diastereomers of pachastrissamine was achieved. Natural pachastrissamine was synthesized through bis-tosylation of the common intermediate and cyclization. 2-epi-Pachastrissamine was obtained by monotosylation and spontaneous cyclization of D-ribo-phytosphingosine derivative. By use of regio- and stereospecific ring-opening reaction of the orthoester assisted by a Bee group as a key step, 3-epi- and 2,3-epi-pachastrissamines were synthesized. The three stereogenic centers of all the diastereomers were constructed by using Garner's aldehyde as the sole chiral source.