[(4aR,8aS)-4,4a,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2-yl] diphenyl phosphate | 250226-75-6

• 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: [(4aR,8aS)-4,4a,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2-yl] diphenyl phosphate
• CAS: 250226-75-6
• 化学式: C₂₀H₂₁O₆P
• 分子量: 388.357
• InChiKey: VXDOYXMXODLVNJ-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(4aR,8aS)-4,4a,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2-yl] diphenyl phosphate 、 在 四(三苯基膦)钯 碳酸氢钠 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 [(2R,3R,4R,5S,6S)-2-[[(4aR,8aS)-4,4a,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2-yl]methyl]-6-[2-(methoxymethoxy)ethyl]-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  A General Method for Convergent Synthesis of Polycyclic Ethers Based on Suzuki Cross-Coupling:  Concise Synthesis of the ABCD Ring System of Ciguatoxin

  摘要：

  [GRAPHICS]A general method for convergent assembly of polyether structure has been developed based on palladium(0)-mediated Suzuki cross-coupling reaction of alkylboranes with cyclic ketene acetal phosphates. The present method allowed for coupling of medium-sited ether rings and thus a concise synthesis of the ABCD ring system of ciguatoxins has been achieved.

  DOI：

  10.1021/ol990885n
• 作为产物：
  描述：

  (2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>methanol 在 palladium dihydroxide 六甲基磷酰三胺 、 pyridine-SO3 complex 、 氢气 、 双(三甲基硅烷基)氨基钾 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 反应 1.0h， 生成 [(4aR,8aS)-4,4a,6,7,8,8a-hexahydropyrano[3,2-b]pyran-2-yl] diphenyl phosphate
  参考文献：
  名称：

  A General Method for Convergent Synthesis of Polycyclic Ethers Based on Suzuki Cross-Coupling:  Concise Synthesis of the ABCD Ring System of Ciguatoxin

  摘要：

  [GRAPHICS]A general method for convergent assembly of polyether structure has been developed based on palladium(0)-mediated Suzuki cross-coupling reaction of alkylboranes with cyclic ketene acetal phosphates. The present method allowed for coupling of medium-sited ether rings and thus a concise synthesis of the ABCD ring system of ciguatoxins has been achieved.

  DOI：

  10.1021/ol990885n

文献信息

• A General Method for Convergent Synthesis of Polycyclic Ethers Based on Suzuki Cross-Coupling:  Concise Synthesis of the ABCD Ring System of Ciguatoxin
  作者：Makoto Sasaki、Haruhiko Fuwa、Makoto Ishikawa、Kazuo Tachibana

  DOI：10.1021/ol990885n

  日期：1999.10.1

  [GRAPHICS]A general method for convergent assembly of polyether structure has been developed based on palladium(0)-mediated Suzuki cross-coupling reaction of alkylboranes with cyclic ketene acetal phosphates. The present method allowed for coupling of medium-sited ether rings and thus a concise synthesis of the ABCD ring system of ciguatoxins has been achieved.