Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester | 186265-11-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester
• 英文别名: 4-oxo-4-[[(1R,4R,5S,7R,8S)-9-oxo-7-pentyl-7-phenylmethoxy-2,6,10-trioxatricyclo[6.3.0.01,5]undecan-4-yl]oxy]butanoic acid
• CAS: 186265-11-2
• 化学式: C₂₄H₃₀O₉
• 分子量: 462.497
• InChiKey: OMZUCGYHSPNQTR-WXJRWHARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester
  参考文献：
  名称：

  Synthesis of syringolide 1 ketals and esters for receptor studies

  摘要：

  The syringolides, specified by avirulence gene D from Pseudomonas syringae, elicit a disease defense reaction only in soybean cultivars carrying the Rpg4 disease resistance gene. In order to identify structural features important for elicitor activity and construct highly labelled elicitor-active probes, several syringolide esters and ketals were synthesized. Alteration of the C-3 hemiketal group of syringolide 1 abolished elicitor activity, but ester derivatives based on the C-4' hydroxy group all retained activity. [I-125]4'-(2-iodo-3,4,5-trimethoxyphenylacetyl) syringolide 1 was prepared for receptor studies. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0031-9422(96)00530-4
• 作为产物：
  描述：

  syringolide 1 在 4-二甲氨基吡啶 、 Dowex 50W-X₈*HCl 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester
  参考文献：
  名称：

  Synthesis of syringolide 1 ketals and esters for receptor studies

  摘要：

  The syringolides, specified by avirulence gene D from Pseudomonas syringae, elicit a disease defense reaction only in soybean cultivars carrying the Rpg4 disease resistance gene. In order to identify structural features important for elicitor activity and construct highly labelled elicitor-active probes, several syringolide esters and ketals were synthesized. Alteration of the C-3 hemiketal group of syringolide 1 abolished elicitor activity, but ester derivatives based on the C-4' hydroxy group all retained activity. [I-125]4'-(2-iodo-3,4,5-trimethoxyphenylacetyl) syringolide 1 was prepared for receptor studies. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0031-9422(96)00530-4

文献信息

• Synthesis of syringolide 1 ketals and esters for receptor studies
  作者：Tetsu Tsurushima、Sharon L. Midland、Chun-min Zeng、Cheng Ji、James J. Sims、Noel T. Keen

  DOI：10.1016/s0031-9422(96)00530-4

  日期：1996.12

  The syringolides, specified by avirulence gene D from Pseudomonas syringae, elicit a disease defense reaction only in soybean cultivars carrying the Rpg4 disease resistance gene. In order to identify structural features important for elicitor activity and construct highly labelled elicitor-active probes, several syringolide esters and ketals were synthesized. Alteration of the C-3 hemiketal group of syringolide 1 abolished elicitor activity, but ester derivatives based on the C-4' hydroxy group all retained activity. [I-125]4'-(2-iodo-3,4,5-trimethoxyphenylacetyl) syringolide 1 was prepared for receptor studies. Copyright (C) 1996 Elsevier Science Ltd