1-deoxy-1-[(2'S,3'S,4'R)-2'-(N-hexacosanoylamino)-3',4'-dihydroxyoctadecyl]-α-D-galactopyranose | 865586-88-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 1-deoxy-1-[(2'S,3'S,4'R)-2'-(N-hexacosanoylamino)-3',4'-dihydroxyoctadecyl]-α-D-galactopyranose
• 英文别名: α-1C-GalCer；N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]octadecan-2-yl]hexacosanamide
• CAS: 865586-88-5
• 化学式: C₅₀H₉₉NO₈
• 分子量: 842.338
• InChiKey: XFRPSTAXSQEEJA-YBXSCEJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  59
• 可旋转键数：
  43
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  160
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (R)-1-((heptadec-1-en-3-yloxy)methyl)-4-methoxybenzene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 titanium(IV) isopropylate 、 sodium azide 、 过氧化氢异丙苯 、 三氟化硼乙醚 、 水 、 D-(-)-酒石酸二异丙酯 、 氯化铵 、 三氟乙酸 、 乙硫醇 作用下， 以 甲乙醚 、 二氯甲烷 为溶剂， 反应 115.0h， 生成 1-deoxy-1-[(2'S,3'S,4'R)-2'-(N-hexacosanoylamino)-3',4'-dihydroxyoctadecyl]-α-D-galactopyranose
  参考文献：
  名称：

  Total Synthesis of α-1C-Galactosylceramide, an Immunostimulatory C-Glycosphingolipid, and Confirmation of the Stereochemistry in the First-Generation Synthesis

  摘要：

  A nonisosteric alpha-C-glycoside analogue of KRN7000 (alpha-1C-GalCer, 1) was reported to induce a selective type of cytokine release in human invariant natural killer cells in vitro. We report here a very concise synthetic route to 1 and its analogue 1'. The key steps include olefin cross-metathesis, Sharpless asymmetric epoxidation, and epoxide opening by NaN3/NH4Cl. Inversion of configuration at the amide-bearing carbon in the phytosphingosine backbone constructed by epoxide opening in our previous synthesis of 1 was verified, indicating that remote group participation is not involved during the epoxide-opening reaction.

  DOI：

  10.1021/jo201450s

文献信息

• [EN] SYNTHESIS OF DIVERSE GLYCOSYLPHOSPHATIDYLINOSITOL GLYCANS FROM TOXOPLASMA GONDII AND THEIR APPLICATION AS VACCINES AND DIAGNOSTICS<br/>[FR] SYNTHÈSE DE DIVERS GLYCOSYLPHOSPHATIDYLINOSITOL GLYCANES À PARTIR DE TOXOPLASMA GONDII ET LEUR APPLICATION EN TANT QUE VACCINS ET OUTILS DE DIAGNOSTIC
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2014016317A1

  公开（公告）日：2014-01-30

  The present invention relates to the synthesis of GPI-related surface antigens of the parasite Toxoplasma gondii (T. gondii) and the resulting products obtained. These synthetic compounds are suitable for diagnosis of toxoplasmosis, as well as vaccine against toxoplasmosis, a diseases caused by infection with T. gondii.

  本发明涉及寄生虫弓形虫（Toxoplasma gondii，T. gondii）的GPI相关表面抗原的合成以及所得到的产物。这些合成化合物适用于弓形虫病的诊断，以及针对由感染弓形虫引起的疾病弓形虫病的疫苗。
• [EN] SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE SEROTYPE 2<br/>[FR] VACCINS SYNTHÉTIQUES CONTRE LE SÉROTYPE 2 DE STREPTOCOCCUS PNEUMONIAE
  申请人：MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WSS E V

  公开号：WO2017103211A1

  公开（公告）日：2017-06-22

  The present invention relates to a synthetic saccharide of general formula (I) that is related to Streptococcus pneumoniaeserotype 2 capsular polysaccharide, a conjugate thereofand the use of said saccharide and conjugatefor raising a protective immune response in a human and/or animal host. Furthermore, the synthetic saccharide of general formula (I) isuseful as marker in immunological assays fordetection of antibodies against Streptococcus pneumoniaetype 2 bacteria.

  本发明涉及一种与肺炎链球菌2型胶囊多糖相关的一般式(I)的合成糖苷，以及其共轭物和在人类和/或动物宿主中引发保护性免疫应答的用途。此外，一般式(I)的合成糖苷可用作免疫学检测中的标记，用于检测针对肺炎链球菌2型细菌的抗体。
• [EN] SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE TYPE 1<br/>[FR] VACCINS SYNTHÉTIQUES CONTRE LE STREPTOCOCCUS PNEUMONIAE DE TYPE 1
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2015004041A1

  公开（公告）日：2015-01-15

  The present invention relates to the total synthesis of saccharide structures contained in the capsular polysaccharide of Streptococcus pneumoniae type 1, to glycoconjugates containing said saccharide structures obtained by total synthesis and to use of such glycoconjugates and pharmaceutical compositions thereof in the immunization against diseases associated with bacteria containing said saccharide structures in their capsular polysaccharide, and more specifically associated with Streptococcus pneumoniae.

  本发明涉及肺炎链球菌1型胶囊多糖中含有的糖结构的全合成，涉及通过全合成获得含有该糖结构的糖蛋白共轭物，以及利用这种糖蛋白共轭物和制药组合物在免疫过程中用于预防与其胶囊多糖中含有该糖结构的细菌相关的疾病，更具体地与肺炎链球菌相关。
• Synthetic vaccines against Streptococcus pneumoniae
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2845860A1

  公开（公告）日：2015-03-11

  The present invention relates to the total synthesis of saccharide structures contained in the capsular polysaccharide of Streptococcus pneumoniae type 1, to glycoconjugates containing said saccharide structures obtained by total synthesis and to use of such glycoconjugates and pharmaceutical compositions thereof in the immunization against diseases associated with bacteria containing said saccharide structures in their capsular polysaccharide, and more specifically associated with Streptococcus pneumoniae.

  本发明涉及对肺炎链球菌1型胶囊多糖中含有的糖结构进行全合成，以及通过全合成获得含有该糖结构的糖蛋白结合物，以及利用这种糖蛋白结合物和其制剂在免疫接种中用于预防与含有这种糖结构的细菌相关的疾病，更具体地与肺炎链球菌相关。
• [EN] VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE SEROTYPE 8<br/>[FR] VACCINS CONTRE STREPTOCOCCUS PNEUMONIAE SÉROTYPE 8
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2016046420A1

  公开（公告）日：2016-03-31

  The present invention relates to synthetic saccharides of general formula (I) that are related to Streptococcuspneumoniae serotype 8 capsular polysaccharide, conjugates thereof and the use of said saccharides and conjugates for raising a protective immune response in a human and/or animal host. Furthermore, the synthetic saccharide structures of general formula (I) are useful as marker in immunological assays for detection of antibodies against Streptococcuspneumoniae bacteria.

  本发明涉及一般式（I）的合成糖苷，与肺炎链球菌8型蒽聚糖有关，以及它们的结合物，以及利用所述糖苷和结合物在人类和/或动物宿主中引发保护性免疫反应。此外，一般式（I）的合成糖苷结构可用作免疫学检测中的标记，用于检测针对肺炎链球菌细菌的抗体。