(4S,6R)-4-(2-acetoxyethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane | 146367-52-4

• 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-acetoxyethyl)-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]ethyl acetate
• CAS: 146367-52-4
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: NLCKCVNXZWLEGO-SJORKVTESA-N

物化性质

• 沸点：
  387.2±17.0 °C(predicted)
• 密度：
  1.023±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,6R)-4-(2-acetoxyethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane 在 sodium 作用下， 以 甲醇 为溶剂， 以98%的产率得到(4S,6R)-4-(2-hydroxyethyl)-6-(2-phenylethyl)-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Polyhydroxylated chiral building block by enzymic desymmetrization of meso 1,3 syn diols

  摘要：

  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.

  DOI：

  10.1021/jo00056a002
• 作为产物：
  描述：

  (4R,6S)-2,2-dimethyl-1,3-dioxane-4,6-diyl-bis-ethane-2,1-diyl diacetate 在 吡啶 、 sodium hydroxide 、 phosphate buffer 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 8.0h， 生成 (4S,6R)-4-(2-acetoxyethyl)-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

• Empirical Model for the Molar Rotations of <i>syn</i>-2,2-Dimethyl-1,3-dioxanes
  作者：Christopher D. Anderson、Scott D. Rychnovsky

  DOI：10.1021/ol0263550

  日期：2002.9.1

  [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.