(4S,6R)-4-(2-hydroxyethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane | 91285-72-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,6R)-4-(2-hydroxyethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane
• 英文别名: 2-[(4S,6R)-2,2-dimethyl-6-(2-phenylethyl)-1,3-dioxan-4-yl]ethanol
• CAS: 91285-72-2
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: NLJNWEKQDFCTQJ-CABCVRRESA-N

物化性质

• 沸点：
  374.5±17.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (4S,6R)-4-(2-hydroxyethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane 在 咪唑 、 溴 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以83%的产率得到(4R,6R)-4-(2-bromoethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Empirical Model for the Molar Rotations of syn-2,2-Dimethyl-1,3-dioxanes

  摘要：

  [GRAPHICS]A useful method for the prediction of molar rotation ([Phi]) of syn-2,2-dimethyl-1,3-dioxanes (acetonides) is described. A series of acetonides were prepared by standard methods. A simple additive relationship between the substituents (R, R') and molar rotation was realized.

  DOI：

  10.1021/ol0263550
• 作为产物：
  描述：

  2,2'-((4R,6S)-2,2-dimethyl-1,3-dioxane-4,6-diyl)bis(ethan-1-ol) 在 吡啶 、 sodium hydroxide 、 phosphate buffer 、 sodium 作用下， 以 甲醇 、 乙醚 、 氯仿 为溶剂， 反应 12.0h， 生成 (4S,6R)-4-(2-hydroxyethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Enzyme-catalyzed desymmetrization of meso-skipped polyols to useful chiral building blocks

  摘要：

  The biocatalytic desymmetrization, in presence of different enzymes, of two models of polyfunctionalized diols in a meso form was studied PFL was found to be the most selective enzyme with excellent results in chemical and optical yield with some of the tested substrates. The obtained chiral building block was utilized for some useful synthetic transformations toward the synthesis of natural products.

  DOI：

  10.1016/s0957-4166(00)80117-2

文献信息

• Synthetic studies related to compactin and mevinolin: A new synthesis of the lactone system.
  作者：Marek Majewski、Derrick L.J. Clive、Paul C. Anderson

  DOI：10.1016/s0040-4039(01)81171-0

  日期：1984.1

  (S)-Malic acid diethyl ester was converted into a precursor of the lactonic portion of compactin and mevinolin. The substance was coupled with benzyl -tolyl sulfone and elaborated into the chiral lactone system of the natural products.

  将（S）-苹果酸二乙酯转化为紧密蛋白和美维林的内酯部分的前体。将该物质与苄基甲苯基砜偶联，并制成天然产物的手性内酯体系。
• Polyhydroxylated chiral building block by enzymic desymmetrization of meso 1,3 syn diols
  作者：Carlo Bonini、Rocco Racioppi、Giuliana Righi、Licia Viggiani

  DOI：10.1021/jo00056a002

  日期：1993.2

  A new seven-carbon polyhydroxylated chiral synthon is obtained, as single enantiomer, in nearly quantitative yield by enzymatic desymmetrization of the appropriate meso compound. Pseudomonas fluorescens shows an high degree of enantiotopic discrimination in a particularly complex molecule possessing a 1,3 syn diol structure; likewise, this chiral synthon has been easily transformed into a known compactin analogue.