(+)-S-2-pyridyl (2S,3S,6R,8S)-8-O-((2'R,3'R,6'S,8'R)-8'-O'-{(2S,3S,6R,8S)-8-O-[(2R,3R,6S,8R)-bishomononactoyl]bishomononactoyl}bishomononactoyl)thiobishomononactate | 1332849-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (+)-S-2-pyridyl (2S,3S,6R,8S)-8-O-((2'R,3'R,6'S,8'R)-8'-O'-{(2S,3S,6R,8S)-8-O-[(2R,3R,6S,8R)-bishomononactoyl]bishomononactoyl}bishomononactoyl)thiobishomononactate
• CAS: 1332849-16-7
• 化学式: C₅₃H₈₅NO₁₂S
• 分子量: 960.323
• InChiKey: XAMSYOPGLKCFLY-KVTBGRSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.72
• 重原子数：
  67.0
• 可旋转键数：
  24.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  166.01
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (+)-S-2-pyridyl (2S,3S,6R,8S)-8-O-((2'R,3'R,6'S,8'R)-8'-O'-{(2S,3S,6R,8S)-8-O-[(2R,3R,6S,8R)-bishomononactoyl]bishomononactoyl}bishomononactoyl)thiobishomononactate 在 silver perchlorate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以81%的产率得到macrotetrolide α
  参考文献：
  名称：

  Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids

  摘要：

  Macrotetrolide alpha (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.012
• 作为产物：
  描述：

  (S)-2-{(2S,5R)-5-[(S)-2-((R)-2-{(2R,5S)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyl]-tetrahydro-furan-2-yl}-propionyloxy)-3-methyl-butyl]-tetrahydro-furan-2-yl}-propionic acid 在 palladium 10% on activated carbon 、 氢氟酸 、 氢气 、 silver perchlorate 、 三苯基膦 作用下， 以 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 30.08h， 生成 (+)-S-2-pyridyl (2S,3S,6R,8S)-8-O-((2'R,3'R,6'S,8'R)-8'-O'-{(2S,3S,6R,8S)-8-O-[(2R,3R,6S,8R)-bishomononactoyl]bishomononactoyl}bishomononactoyl)thiobishomononactate
  参考文献：
  名称：

  Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids

  摘要：

  Macrotetrolide alpha (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.012