(3aR,4S,6S,6aR)-6-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate | 1551543-45-3

• 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: (3aR,4S,6S,6aR)-6-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate
• 英文别名: [(3aR,4S,6S,6aR)-6-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl] benzoate
• CAS: 1551543-45-3
• 化学式: C₁₆H₂₀O₇
• 分子量: 324.331
• InChiKey: PLSNIXVDOYJYQS-OKWIKPQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,4S,6S,6aR)-6-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate 在 sodium periodate 、 copper(I) bromide dimethylsulfide complex 、 二甲基硫 、 Dimethylsulfonium-dichlorid 、 水 、 silica gel 、 双(三甲基硅烷基)氨基钾 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 32.5h， 生成 (4R,5R)-2,2-dimethyl-5-((R,E)-3-methylhexa-1,5-dien-1-yl)-1,3-dioxolane-4-carboxylic acid
  参考文献：
  名称：

  A Concise Synthesis of Carolacton

  摘要：

  A synthesis of carolacton, a myxobacterial natural product that has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear sequence of 14 steps from an Evans beta-ketoimide and enabled preliminary evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further investigations into carolacton's structure function relationships are warranted.

  DOI：

  10.1021/ol500004k
• 作为产物：
  描述：

  (3aR,4S,6S,6aR)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 20.0h， 以99%的产率得到(3aR,4S,6S,6aR)-6-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl benzoate
  参考文献：
  名称：

  A Concise Synthesis of Carolacton

  摘要：

  A synthesis of carolacton, a myxobacterial natural product that has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear sequence of 14 steps from an Evans beta-ketoimide and enabled preliminary evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further investigations into carolacton's structure function relationships are warranted.

  DOI：

  10.1021/ol500004k

文献信息

• A Concise Synthesis of Carolacton
  作者：Michal S. Hallside、Richard S. Brzozowski、William M. Wuest、Andrew J. Phillips

  DOI：10.1021/ol500004k

  日期：2014.2.21

  A synthesis of carolacton, a myxobacterial natural product that has profound effects on Streptococcus mutans biofilms, is reported. The synthesis proceeds via a longest linear sequence of 14 steps from an Evans beta-ketoimide and enabled preliminary evaluations of the effects of late-stage intermediates on S. mutans biofilms. These studies suggest that further investigations into carolacton's structure function relationships are warranted.