6-(1-hydroxyallyl)-3-methyl-2-propenyltetrahydropyran-4-ol | 331686-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 6-(1-hydroxyallyl)-3-methyl-2-propenyltetrahydropyran-4-ol
• 英文别名: (2S,3S,4R,6S)-6-[(1R)-1-hydroxyprop-2-enyl]-3-methyl-2-[(E)-prop-1-enyl]oxan-4-ol
• CAS: 331686-86-3
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: QJRISYYFWACLKJ-DPUITWOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(1-hydroxyallyl)-3-methyl-2-propenyltetrahydropyran-4-ol 在 palladium diacetate 吡啶 、 2,6-二甲基吡啶 、 manganese(IV) oxide 、 四丁基溴化铵 、 4-甲基苯磺酸吡啶 、 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 39.0h， 生成 (R)-6-{(1E,3Z,7E,9E)-(5R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-11-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  The First Total Synthesis of (+)-Ratjadone

  摘要：

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.

  DOI：

  10.1021/jo005768g
• 作为产物：
  描述：

  [(2S,3R,4R,6S)-6-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]-3-methyl-2-[(E)-prop-1-enyl]oxan-4-yl]oxy-tert-butyl-dimethylsilane 在 盐酸 、 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 31.25h， 生成 6-(1-hydroxyallyl)-3-methyl-2-propenyltetrahydropyran-4-ol
  参考文献：
  名称：

  The First Total Synthesis of (+)-Ratjadone

  摘要：

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.

  DOI：

  10.1021/jo005768g

文献信息

• Diastereoselective Synthesis of 2,3,6-Trisubstituted Tetrahydropyran-4-ones via Prins Cyclizations of Enecarbamates: A Formal Synthesis of (+)-Ratjadone A
  作者：Kimberly N. Cossey、Raymond L. Funk

  DOI：10.1021/ja046940r

  日期：2004.10.1

  precursors by alkylation of metalated (E)-enecarbamates with epoxides. The stereochemistry of the resultant trisubstituted (E)-enecarbamates is then transferred with high fidelity to afford the frequently observed and biologically significant all-cis-2,3,6-trisubstituted tetrahydropyran substructures of naturally occurring compounds. Other substituted tetrahydropyrans, including 2,3,5,6-tetrasubstituted

  烯氨基甲酸酯被证明是 Prins 环化的极好终止基团。这种方法的一个值得注意的特点是通过金属化 (E)-烯氨基甲酸酯与环氧化物的烷基化，可以轻松、立体选择性地构建环化前体。然后以高保真度转移所得三取代 (E)-烯氨基甲酸酯的立体化学，以提供经常观察到且具有生物学意义的天然化合物的全顺-2,3,6-三取代四氢吡喃亚结构。其他取代的四氢吡喃，包括 2,3,5,6-四取代、顺-2,3-二取代和顺-2,6-二取代，也可使用。这种方法促进了核输出抑制剂 (+)-ratjadone A 的异常简洁的正式全合成。
• The First Total Synthesis of (+)-Ratjadone
  作者：Ulhas Bhatt、Mathias Christmann、Monika Quitschalle、Eckhard Claus、Markus Kalesse

  DOI：10.1021/jo005768g

  日期：2001.3.1

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.