N-[(2R,4aR,6S,7S,8R,8aS)-6-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-methyl-4,5-bis(phenylmethoxy)-2-prop-2-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide | 218607-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,4aR,6S,7S,8R,8aS)-6-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-methyl-4,5-bis(phenylmethoxy)-2-prop-2-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 218607-51-3
• 化学式: C₇₂H₇₉NO₁₅
• 分子量: 1198.42
• InChiKey: FRZOYCYSAHHQDW-ZOOFIELSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  88
• 可旋转键数：
  28
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N-[(2R,4aR,6S,7S,8R,8aS)-6-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-methyl-4,5-bis(phenylmethoxy)-2-prop-2-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide 在 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  19F型肺炎链球菌的荚膜多糖：重复单元的合成。

  摘要：

  β-D-ManpNAc-（1-> 4）-alpha-D-Glcp-（1-> 2）-alpha-L-Rhap（一种肺炎链球菌型三糖重复单元）的新型合成方法描述了19F荚膜多糖。本方法允许通过选择性地操纵还原端的异头位置和非还原端的HO-4功能来简单地获得含有三糖的不同片段，并使产物与蛋白质缀合。合成方案显示了亚砜方法对于糖苷键的立体选择性和高产率形成的有效应用。

  DOI：

  10.1016/s0008-6215(98)00218-3
• 作为产物：
  描述：

  乙酸酐 、 (2R,4aR,6S,7S,8R,8aS)-7-azido-6-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-methyl-4,5-bis(phenylmethoxy)-2-prop-2-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine 在 copper(II) sulfate 、 锌 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 2.0h， 以84%的产率得到N-[(2R,4aR,6S,7S,8R,8aS)-6-[(2R,3R,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-methyl-4,5-bis(phenylmethoxy)-2-prop-2-enoxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
  参考文献：
  名称：

  19F型肺炎链球菌的荚膜多糖：重复单元的合成。

  摘要：

  β-D-ManpNAc-（1-> 4）-alpha-D-Glcp-（1-> 2）-alpha-L-Rhap（一种肺炎链球菌型三糖重复单元）的新型合成方法描述了19F荚膜多糖。本方法允许通过选择性地操纵还原端的异头位置和非还原端的HO-4功能来简单地获得含有三糖的不同片段，并使产物与蛋白质缀合。合成方案显示了亚砜方法对于糖苷键的立体选择性和高产率形成的有效应用。

  DOI：

  10.1016/s0008-6215(98)00218-3

文献信息

• Synthesis of phosphorylated fragments of Streptococcus pneumoniae type 19F capsular polysaccharide
  作者：Giuseppina Soliveri、Anna Bertolotti、Luigi Panza、Laura Poletti、Christopher Jones、Luigi Lay

  DOI：10.1039/b205684d

  日期：2002.10.1

  Serotype 19F is one of the most virulent of the Streptococcus pneumoniae serotypes, causing meningitis, otitis media, septicemia and pneumonia. Effective protection against infection is mediated by antibodies directed against its capsular polysaccharide (CPS), composed of the trisaccharide repeating units (→4-β-D-ManpNAc-(1→4)-α-D-Glcp-(1→2)-α-L-Rhap-1→) bridged by phosphate diesters. Unfortunately, CPSs are typical T-independent type 2 immunogens. Therefore, the conjugation of putative saccharide haptens to a protein carrier, which invokes T-cell involvement, has proved to be extremely effective in enhancing the immune response. In a project aimed at ascertaining the role played by the different structural factors in the immunogenicity of new vaccines against Streptococcus pneumoniae type 19F, we planned the synthesis of a family of trisaccharide repeating unit derivatives where the phosphate group is a) absent; b) linked only to the rhamnose unit; or c) linked only to the N-acetylmannosamine unit. Compound of type a) and c) also bear an appropriate spacer for conjugation to the protein carrier. Moreover, the synthesis of a dimer of the CPS repeating unit, in which a phosphate diester bridges two repeating units, was carried out.

  血清型19F是肺炎链球菌中最具毒力的血清型之一，能够引起脑膜炎、中耳炎、脓毒血症和肺炎。对感染的有效保护是通过针对其荚膜多糖（CPS）的抗体介导的，该多糖由三糖重复单元（→4-β-D-ManpNAc-(1→4)-α-D-Glcp-(1→2)-α-L-Rhap-1→）通过磷酸二酯桥接而成。不幸的是，CPS通常是T细胞非依赖性2型免疫原。因此，将假定的糖类半抗原与蛋白质载体结合，以激发T细胞参与，已被证明在增强免疫应答方面极为有效。在一个旨在确定不同结构因素在新疫苗对肺炎链球菌19F型免疫原性中所起作用的项目中，我们计划合成一系列三糖重复单元衍生物，其中磷酸基团a) 缺失；b) 仅与鼠李糖单元相连；或c) 仅与N-乙酰甘露糖胺单元相连。a型和c型化合物还带有适当的连接 spacer，以便与蛋白质载体结合。此外，还进行了CPS重复单元二聚体的合成，其中磷酸二酯桥接两个重复单元。
• Capsular polysaccharide of Streptococcus pneumoniae type 19F: synthesis of the repeating unit
  作者：Ennio Bousquet、Malika Khitri、Luigi Lay、Francesco Nicotra、Luigi Panza、Giovanni Russo

  DOI：10.1016/s0008-6215(98)00218-3

  日期：1998.10

  A new and more versatile synthesis of beta-D-ManpNAc-(1-->4)-alpha-D-Glcp-(1-->2)-alpha-L-Rhap, the trisaccharide repeating unit of the Streptococcus pneumoniae type 19F capsular polysaccharide, is described. The present approach allows a simple access to different fragments containing the trisaccharide and the conjugation of the product(s) to a protein through the selective manipulation of the anomeric

  β-D-ManpNAc-（1-> 4）-alpha-D-Glcp-（1-> 2）-alpha-L-Rhap（一种肺炎链球菌型三糖重复单元）的新型合成方法描述了19F荚膜多糖。本方法允许通过选择性地操纵还原端的异头位置和非还原端的HO-4功能来简单地获得含有三糖的不同片段，并使产物与蛋白质缀合。合成方案显示了亚砜方法对于糖苷键的立体选择性和高产率形成的有效应用。