(2S,3R,4aS,5aR,7S,8R,9aS,11aR)-7-Benzyloxy-8-benzyloxymethyl-2-hydroxymethyl-2,11a-dimethyl-dodecahydro-1,5,9-trioxa-dibenzo[a,d]cyclohepten-3-ol | 632354-64-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4aS,5aR,7S,8R,9aS,11aR)-7-Benzyloxy-8-benzyloxymethyl-2-hydroxymethyl-2,11a-dimethyl-dodecahydro-1,5,9-trioxa-dibenzo[a,d]cyclohepten-3-ol
• 英文别名: (1R,3S,5R,6S,8R,11S,13R,14S)-6-(hydroxymethyl)-6,8-dimethyl-14-phenylmethoxy-13-(phenylmethoxymethyl)-2,7,12-trioxatricyclo[9.4.0.03,8]pentadecan-5-ol
• CAS: 632354-64-4
• 化学式: C₃₀H₄₀O₇
• 分子量: 512.643
• InChiKey: RBJPNLOMHCVLDF-HYJOMICCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4aS,5aR,7S,8R,9aS,11aR)-7-Benzyloxy-8-benzyloxymethyl-2-hydroxymethyl-2,11a-dimethyl-dodecahydro-1,5,9-trioxa-dibenzo[a,d]cyclohepten-3-ol 在 palladium dihydroxide 2,6-二甲基吡啶 、 ruthenium(IV) oxide 、 sodium periodate 、 正丁基锂 、 camphor-10-sulfonic acid 、 氢气 、 4-甲基苯磺酸吡啶 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 19.5h， 生成 (1S,3R,5S,7R,8S,10R,13S,15R,17S,19R,21S,22R,24S,26R)-8-(hydroxymethyl)-8,10,22-trimethyl-21-phenylmethoxy-22-(2-phenylmethoxyethyl)-4,9,14,18,23,27-hexaoxahexacyclo[13.12.0.03,13.05,10.017,26.019,24]heptacosan-7-ol
  参考文献：
  名称：

  Sulfonyl-Stabilized Oxiranyllithium-Based Approach to Polycyclic Ethers. Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, marine polycyclic ether toxins causative of diarrheic shellfish poisoning, has been accomplished. The A-ring fragment was constructed by coupling of an appropriately functionalized sulfonyl-stabilized oxiranyl anion and a triflate prepared from an erythritol derivative. An iterative protocol of the oxiranyl anion strategy was also applied for the construction of the DEF-ring fragment. The triflate derivatives of the A-ring and the DEF-ring fragments were connected with lithium acetylide. The resulting acetylene derivative was further transformed into the hexacyclic ABCDEF fragment via oxidation of the acetylene unit to 1,2-diketone, double methyl acetal formation, and reductive etherification.

  DOI：

  10.1021/jo035145d
• 作为产物：
  描述：

  (2S,3R,4aS,5aR,7S,8R,9aS,11aR)-7-benzyloxy-8-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)-2,11a-dimethyldodecahydro-1,5,9-trioxadibenzo[a,d]cyclohepten-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以100%的产率得到(2S,3R,4aS,5aR,7S,8R,9aS,11aR)-7-Benzyloxy-8-benzyloxymethyl-2-hydroxymethyl-2,11a-dimethyl-dodecahydro-1,5,9-trioxa-dibenzo[a,d]cyclohepten-3-ol
  参考文献：
  名称：

  Sulfonyl-Stabilized Oxiranyllithium-Based Approach to Polycyclic Ethers. Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, marine polycyclic ether toxins causative of diarrheic shellfish poisoning, has been accomplished. The A-ring fragment was constructed by coupling of an appropriately functionalized sulfonyl-stabilized oxiranyl anion and a triflate prepared from an erythritol derivative. An iterative protocol of the oxiranyl anion strategy was also applied for the construction of the DEF-ring fragment. The triflate derivatives of the A-ring and the DEF-ring fragments were connected with lithium acetylide. The resulting acetylene derivative was further transformed into the hexacyclic ABCDEF fragment via oxidation of the acetylene unit to 1,2-diketone, double methyl acetal formation, and reductive etherification.

  DOI：

  10.1021/jo035145d

文献信息

• Sulfonyl-Stabilized Oxiranyllithium-Based Approach to Polycyclic Ethers. Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin
  作者：Yuji Mori、Kouichi Nogami、Hiasafumi Hayashi、Ryoji Noyori

  DOI：10.1021/jo035145d

  日期：2003.11.1

  Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, marine polycyclic ether toxins causative of diarrheic shellfish poisoning, has been accomplished. The A-ring fragment was constructed by coupling of an appropriately functionalized sulfonyl-stabilized oxiranyl anion and a triflate prepared from an erythritol derivative. An iterative protocol of the oxiranyl anion strategy was also applied for the construction of the DEF-ring fragment. The triflate derivatives of the A-ring and the DEF-ring fragments were connected with lithium acetylide. The resulting acetylene derivative was further transformed into the hexacyclic ABCDEF fragment via oxidation of the acetylene unit to 1,2-diketone, double methyl acetal formation, and reductive etherification.