[(1R,3S,4R,5R,7R)-4-methyl-3-[(E)-2-phenylethenyl]-2,6-dioxabicyclo[3.2.1]octan-7-yl]methanol | 913066-81-6

• 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: [(1R,3S,4R,5R,7R)-4-methyl-3-[(E)-2-phenylethenyl]-2,6-dioxabicyclo[3.2.1]octan-7-yl]methanol
• CAS: 913066-81-6
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: RMMHVLKBVGDPAA-PMEWQSCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1R,3S,4R,5R,7R)-4-methyl-3-[(E)-2-phenylethenyl]-2,6-dioxabicyclo[3.2.1]octan-7-yl]methanol 在 三氧化硫吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (1R,3S,4R,5R,7S)-4-methyl-3-[(E)-2-phenylethenyl]-2,6-dioxabicyclo[3.2.1]octane-7-carbaldehyde
  参考文献：
  名称：

  (+)-Sorangicin A 的特征二氧杂双环 [3.2.1] 辛烷核心的高效第二代合成和 (Z,Z,E)-三烯酸系统的制备

  摘要：

  (+)-sorangicin A ( 1 )的特征二氧杂双环 [3.2.1] 辛烷核心的高效第二代合成，结合有效的立体控制协议，以达到必要的 ( Z , Z , E )-开发了三烯酸体系。核心结构的亮点包括三组分结合、KHMDS 促进的环氧化物环形成-开环级联、Takai 烯化和化学选择性 Sharpless 二羟基化。然后通过与 ( Z , Z )-5-三丁基甲锡烷基-2,4-戊二烯酸乙酯的 Stille 交叉偶联实现三烯酸系统的组装，然后通过温和水解保持三烯构型。

  DOI：

  10.1021/ol802942j
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 [(1R,3S,4R,5R,7R)-4-methyl-3-[(E)-2-phenylethenyl]-2,6-dioxabicyclo[3.2.1]octan-7-yl]methanol
  参考文献：
  名称：

  Synthesis of the C29−C37 Bicyclic Ether Core of (+)-Sorangicin A

  摘要：

  Construction of the unique bicyclic bis-ether core of the macrolide (+)-sorangicin A has been achieved. This fragment was prepared by utilizing a one-pot cascade of three bond forming events. An epoxide opening of the epoxy tosylate 2 led to the formation of the tetrahydropyran and subsequently to a second epoxide. Finally, a second epoxide opening closed the tetrahydrofuran ring. The bicyclic fragment was synthesized in just nine steps from (E)-cinnamaldehyde.

  DOI：

  10.1021/ol061339e

文献信息

• Formal Synthesis of (+)-Sorangicin A
  作者：Michael T. Crimmins、Matthew W. Haley、Elizabeth A. O’Bryan

  DOI：10.1021/ol201920j

  日期：2011.9.2

  The formal synthesis of (+)-sorangicin A was completed by two independent routes. Both approaches feature a cross metathesis reaction to form the C29-C30 bond to arrive at the bicyclic ether/tetrahydropyran fragment. Formation of the C15-C16 olefin to unite the dihydropyran fragment with the rest of the molecule was achieved by either a cross metathesis reaction or a Julia-Kocienski olefination.
• An Efficient, Second-Generation Synthesis of the Signature Dioxabicyclo[3.2.1]octane Core of (+)-Sorangicin A and Elaboration of the (<i>Z</i>,<i>Z</i>,<i>E</i>)-Triene Acid System
  作者：Amos B. Smith,、Shuzhi Dong

  DOI：10.1021/ol802942j

  日期：2009.3.5

  An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A (1), in conjunction with an effective, stereocontrolled protocol to arrive at the requisite (Z,Z,E)-triene acid system has been developed. Highlights of the core construction entail a three-component union, a KHMDS-promoted epoxide ring formation−ring opening cascade, a Takai olefination, and

  (+)-sorangicin A ( 1 )的特征二氧杂双环 [3.2.1] 辛烷核心的高效第二代合成，结合有效的立体控制协议，以达到必要的 ( Z , Z , E )-开发了三烯酸体系。核心结构的亮点包括三组分结合、KHMDS 促进的环氧化物环形成-开环级联、Takai 烯化和化学选择性 Sharpless 二羟基化。然后通过与 ( Z , Z )-5-三丁基甲锡烷基-2,4-戊二烯酸乙酯的 Stille 交叉偶联实现三烯酸系统的组装，然后通过温和水解保持三烯构型。
• Synthesis of the C29−C37 Bicyclic Ether Core of (+)-Sorangicin A
  作者：Michael T. Crimmins、Matthew W. Haley

  DOI：10.1021/ol061339e

  日期：2006.9

  Construction of the unique bicyclic bis-ether core of the macrolide (+)-sorangicin A has been achieved. This fragment was prepared by utilizing a one-pot cascade of three bond forming events. An epoxide opening of the epoxy tosylate 2 led to the formation of the tetrahydropyran and subsequently to a second epoxide. Finally, a second epoxide opening closed the tetrahydrofuran ring. The bicyclic fragment was synthesized in just nine steps from (E)-cinnamaldehyde.