ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside | 182167-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside
• CAS: 182167-81-3
• 化学式: C₂₂H₂₄O₅S
• 分子量: 400.496
• InChiKey: GLBXKCFOZUUSFO-JHGBEIFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside 在 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 3.25h， 生成 Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Preparation of Disaccharide Haptens Corresponding toSalmonellaSerogroups B and D

  摘要：

  The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelo-pyranoside 26 were prepared by a sequence of reactions, the key step of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compounds 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(alpha-D-abequopyranosyl)-alpha-D-mannopyranoside 1 and allyl 3-O-(alpha-D-tyvelopyranosyl)-alpha-D-mannopyranoside 2.

  DOI：

  10.1080/07328309608005684
• 作为产物：
  描述：

  Benzoic acid (2S,3S,5S,6R)-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yl ester 在 吡啶 、 硫酸 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  Preparation of Disaccharide Haptens Corresponding toSalmonellaSerogroups B and D

  摘要：

  The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelo-pyranoside 26 were prepared by a sequence of reactions, the key step of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compounds 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(alpha-D-abequopyranosyl)-alpha-D-mannopyranoside 1 and allyl 3-O-(alpha-D-tyvelopyranosyl)-alpha-D-mannopyranoside 2.

  DOI：

  10.1080/07328309608005684

文献信息

• Synthesis of and molecular dynamics simulations on a tetrasaccharide corresponding to the repeating unit of the capsular polysaccharide from Salmonella enteritidis
  作者：Johan D. M. Olsson、Jens Landström、Jerk Rönnols、Stefan Oscarson、Göran Widmalm

  DOI：10.1039/b823428k

  日期：——

  Syntheses of two oligosaccharides as methyl glycosides related to the repeating unit of S. enteritidis capsular polysaccharide (CPS) are presented. The trisaccharide corresponds to the backbone of the CPS whereas the tetrasaccharide is a model for the repeating unit which has a branched structure. Molecular dynamics simulations investigating their flexibility and dynamics revealed that the oligosaccharides

  提出了两种寡糖的合成，它们是与肠炎沙门氏菌荚膜多糖（CPS）的重复单元有关的甲基糖苷。三糖对应于CPS的主链，而四糖是具有分支结构的重复单元的模型。分子动力学模拟研究其灵活性和动力学表明，寡糖填充了几种构象状态，并表明构象平均应用于描述可及的构象空间。