(4aR,8aS)-Hexahydro-pyrano[3,2-b]pyran-2-one | 250226-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4aR,8aS)-Hexahydro-pyrano[3,2-b]pyran-2-one
• CAS: 250226-92-7；60378-39-4
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: BPYDYQQKJTYIAB-RQJHMYQMSA-N

物化性质

• 沸点：
  314.5±35.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4aR,8aS)-Hexahydro-pyrano[3,2-b]pyran-2-one 在 四(三苯基膦)钯 六甲基磷酰三胺 、 双(三甲基硅烷基)氨基钾 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 21.0h， 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 pyridine-SO3 complex 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 生成 (4aR,8aS)-Hexahydro-pyrano[3,2-b]pyran-2-one
  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

• New strategy for convergent synthesis of trans-fused polyether frameworks based on palladium-catalyzed suzuki cross-coupling reaction
  作者：Makoto Sasaki、Haruhiko Fuwa、Masayuki Inoue、Kazuo Tachibana

  DOI：10.1016/s0040-4039(98)02025-5

  日期：1998.12

  A new strategy for convergent synthesis of trans-fused polyethers based on palladium(0)-catalyzed Suzuki cross-coupling reaction of alkylboranes with cyclic enol triflates has been developed. The present method allows to construct polyether frameworks rapidly and efficiently.

  基于钯（0）催化烷基硼烷与环烯醇三氟甲磺酸酯的Suzuki交叉偶联反应，开发了一种聚合合成反式聚醚的新策略。本方法允许快速和有效地构建聚醚框架。
• Methods for pyranoannulation: an approach to a new class of polyethers
  作者：Alan P. Kozikowski、Arun K. Ghosh

  DOI：10.1021/jo00216a049

  日期：1985.8

  Several methods have been developed for fusing a pyran ring to an existing pyran ring structure such that the ring oxygens assume a vicinal (ethylene glycol) relationship. The tricyclic structure 13, a previously unknown substance, was prepared through a combination of these methods.
• 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.