(E)-ethyl 3-((3aR,5R,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)acrylate | 133391-32-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-ethyl 3-((3aR,5R,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)acrylate
• 英文别名: ethyl (E)-3-[(3aR,5R,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]prop-2-enoate
• CAS: 133391-32-9
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: VKYDVVACWMQOTM-CSERLTPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-((3aR,5R,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)acrylate 在 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 potassium carbonate 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 72.0h， 以92%的产率得到(2R,3R)-ethyl 2,3-dihydroxy-3-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)propanoate
  参考文献：
  名称：

  Spirastrellolide B: The Synthesis of Southern (C₉−C₂₅) Region

  摘要：

  A combination of ''chiron" and "asymmetric" approaches is utilized to construct the southern (C-9-C-25) region of marine natural product spirastrellolide B. The key functionalities are derived from D-glucose and Sharpless asymmetric epoxidation and dihydroxylation.

  DOI：

  10.1021/ol801771s
• 作为产物：
  描述：

  3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-pentodialdo-1,4-furanose 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 2.0h， 以6.80 g的产率得到(E)-ethyl 3-((3aR,5R,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)acrylate
  参考文献：
  名称：

  Spirastrellolide B: The Synthesis of Southern (C₉−C₂₅) Region

  摘要：

  A combination of ''chiron" and "asymmetric" approaches is utilized to construct the southern (C-9-C-25) region of marine natural product spirastrellolide B. The key functionalities are derived from D-glucose and Sharpless asymmetric epoxidation and dihydroxylation.

  DOI：

  10.1021/ol801771s

文献信息

• TADANO, KIN-ICHI;SHIMADA, KEI-ICHI;ISHIHARA, JUN;OGAWA, SEIICHIRO, J. CARBOHYDR. CHEM., 10,(1991) N, C. 1-9
  作者：TADANO, KIN-ICHI、SHIMADA, KEI-ICHI、ISHIHARA, JUN、OGAWA, SEIICHIRO

  DOI：——

  日期：——
• Spirastrellolide B: The Synthesis of Southern (C₉−C₂₅) Region
  作者：Srivari Chandrasekhar、Chegondi Rambabu、Annareddy Syamprasad Reddy

  DOI：10.1021/ol801771s

  日期：2008.10.2

  A combination of ''chiron" and "asymmetric" approaches is utilized to construct the southern (C-9-C-25) region of marine natural product spirastrellolide B. The key functionalities are derived from D-glucose and Sharpless asymmetric epoxidation and dihydroxylation.