2-[(4S,6R)-2,2-dimethyl-6-[2-(4-methylphenyl)sulfonyloxyethyl]-1,3-dioxan-4-yl]ethyl acetate | 152419-73-3

• 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: 2-[(4S,6R)-2,2-dimethyl-6-[2-(4-methylphenyl)sulfonyloxyethyl]-1,3-dioxan-4-yl]ethyl acetate
• CAS: 152419-73-3
• 化学式: C₁₉H₂₈O₇S
• 分子量: 400.493
• InChiKey: QKIBYXUBKPZEHD-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(4S,6R)-2,2-dimethyl-6-[2-(4-methylphenyl)sulfonyloxyethyl]-1,3-dioxan-4-yl]ethyl acetate 在 sodium 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 7.0h， 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
• 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 、 phosphate buffer 作用下， 以 氯仿 、 水 为溶剂， 反应 5.0h， 生成 2-[(4S,6R)-2,2-dimethyl-6-[2-(4-methylphenyl)sulfonyloxyethyl]-1,3-dioxan-4-yl]ethyl acetate
  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