(1S,3R,4R,5R)-3,4-O-Cyclopentylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one | 164029-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,3R,4R,5R)-3,4-O-Cyclopentylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one
• 英文别名: (1R,2R,6R,8S)-8-hydroxyspiro[3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,1'-cyclopentane]-9-one
• CAS: 164029-68-9
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: WZODKNSAKHPFDW-SDNRWEOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5R)-3,4-O-Cyclopentylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以63%的产率得到(1R,2S,3R,5R)-1,2-O-Cyclopentylidene-1,2,3,5-tetrahydroxy-5-(hydroxymethyl)cyclohexane
  参考文献：
  名称：

  Transformations of Quinic Acid. Asymmetric Synthesis and Absolute Configuration of Mycosporin I and Mycosporin-gly

  摘要：

  D-(-)-Quinic acid (1) was converted to the fungal metabolites mycosporin I (2) and mycosporin-gly (13) via the iminophosphorane 64. The latter was prepared in 10 steps from 1 using oxidative bromination of quinide 33 to furnish 41. Reduction of the gamma-lactone, followed by protection of the 1,2-diol, was accompanied by migration of the benzoyl group to yield 43. The latter was oxidized to 47 which underwent displacement by sulfinate to give 59. O-Methylation, followed by reduction of the benzoate, afforded 61. Oxidation of 61 produced 62 which was converted to beta-azido enone 63. Treatment of 63 with triphenylphosphine gave crystalline 64. An aza-Wittig reaction of 64 with glyoxylate and reduction of the resultant imine yielded 68 which, after deprotection, afforded 13. Analogous coupling of 64 with diethyl ketomalonate and subsequent reduction of the ester groups led to 2. Mycosporin I and mycosporin-gly are shown by this sequence to possess S absolute configuration.

  DOI：

  10.1021/jo00117a008
• 作为产物：
  描述：

  右旋奎宁酸 、 环戊酮 在 硫酸 作用下， 以 丙酮 为溶剂， 生成 (1S,3R,4R,5R)-3,4-O-Cyclopentylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one
  参考文献：
  名称：

  Parallel synthesis and biological evolution of quinic acid derivatives as immuno-suppressing agents against T-cell receptors

  摘要：

  一种对奎尼酸衍生物的并行合成被探索，并研究了它们对T细胞的生物进化。

  DOI：

  10.1039/c5ra06095h

文献信息

• CAFFEOYLQUINIC ACID DERIVATIVES CONTAINING NITROGEN, AND PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USAGE THEREOF
  申请人：Wu Zhanggui

  公开号：US20100144828A1

  公开（公告）日：2010-06-10

  The present invention provides caffeoylquinic acid derivatives and a method of preparing for the same, and also provides pharmaceutical compositions containing caffeoylquinic acid derivatives, and uses of caffeoylquinic acid derivatives in preparation of a medicament for the treatment or prophylaxis of virus diseases, in particular, uses of respiratory syncytial virus and hepatitis B virus, which has the characteristics of safety, high effectiveness and low toxicity.
• US8722725B2
  申请人：——

  公开号：US8722725B2

  公开（公告）日：2014-05-13