(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-hydroxymethyltetrahydropyran-3-ol | 632354-40-6

• 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)-5-benzyloxy-6-benzyloxymethyl-2-hydroxymethyltetrahydropyran-3-ol
• 英文别名: (2S,3R,5S,6R)-2-(hydroxymethyl)-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 632354-40-6
• 化学式: C₂₁H₂₆O₅
• 分子量: 358.434
• InChiKey: HDBHMFRRZUEBNH-IVAOSVALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-hydroxymethyltetrahydropyran-3-ol 在 N-甲基吗啉 、 2,6-二甲基吡啶 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 9.25h， 生成 (E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate
  参考文献：
  名称：

  氧杂环丁基阴离子合成多环醚的收敛策略

  摘要：

  开发了一种新的[X + 2 + Y]型，用于基于环氧乙烷基阴离子策略的多环醚聚合合成。该序列包括用环氧乙烷阴离子随后6-三氟甲磺酸酯的亲核取代内环化，环扩展，和还原醚化。该协议采用灵活的方法来处理由相同原料的六元和七元醚环组成的反式多环阵列。

  DOI：

  10.1021/ol202467z
• 作为产物：
  描述：

  (4aS,6R,7S,8aR)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以88%的产率得到(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-hydroxymethyltetrahydropyran-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

• Divergent Synthesis of Trans-Fused Polycyclic Ethers by a Convergent Oxiranyl Anion Strategy
  作者：Takeo Sakai、Ai Sugimoto、Hiroki Tatematsu、Yuji Mori

  DOI：10.1021/jo302267f

  日期：2012.12.21

  oxiranyl anion generated from an epoxy sulfone, followed by ring expansion, allowed for the incorporation of medium-sized ring ethers into the key intermediate. Subsequent acetal formation and reductive etherification afforded various octacycles containing seven- and eight-membered ether rings.

  对应于耶司毒素CDEFGHIJ环系统的八环聚醚以及G和/或I环修饰的类似物，是使用[X + 2 + Y]型从一种常见的中间体开始，以发散的方式合成的收敛方法。三氟甲磺酸酯与环氧砜产生的环氧乙烷基阴离子反应，然后进行环扩环，从而允许将中等大小的环醚掺入关键中间体中。随后的乙缩醛形成和还原性醚化反应得到了各种八环，其中包含七元和八元醚环。
• A Convergent Strategy for the Synthesis of Polycyclic Ethers by Using Oxiranyl Anions
  作者：Takeo Sakai、Ai Sugimoto、Yuji Mori

  DOI：10.1021/ol202467z

  日期：2011.11.4

  A new [X+2+Y]-type for the convergent synthesis of polycyclic ethers based on an oxiranyl anion strategy was developed. The sequence involves nucleophilic substitution of a triflate with an oxiranyl anion followed by 6-endo cyclization, ring expansion, and reductive etherification. The protocol features a flexible approach toward trans-fused polycyclic arrays consisting of six- and seven-membered ether

  开发了一种新的[X + 2 + Y]型，用于基于环氧乙烷基阴离子策略的多环醚聚合合成。该序列包括用环氧乙烷阴离子随后6-三氟甲磺酸酯的亲核取代内环化，环扩展，和还原醚化。该协议采用灵活的方法来处理由相同原料的六元和七元醚环组成的反式多环阵列。
• 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.