(2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran | 632354-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran
• 英文别名: [(2S,3R,5S,6R)-2-[[(2S,3R)-2-(benzenesulfonyl)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]methyl]-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]oxy-triethylsilane
• CAS: 632354-42-8
• 化学式: C₅₂H₆₆O₈SSi₂
• 分子量: 907.328
• InChiKey: VQEOZIOSJQHQGS-YPMKFMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.87
• 重原子数：
  63
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以82%的产率得到(2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one
  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：

  (1R,6S,8R,9S)-8-benzyloxymethyl-3,3-di-tert-butyl-2,4,7-trioxa-3-silabicyclo[4.4.0]decan-9-ol 在 2,6-二甲基吡啶 、 正丁基锂 、 四丁基氟化铵 、 potassium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran
  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.