biphenyl-4-ylmethyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate | 1336854-09-1

• 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: biphenyl-4-ylmethyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate
• 英文别名: (4-phenylphenyl)methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate
• CAS: 1336854-09-1
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: VZLDNMZWKJSRGN-KBXCAEBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  biphenyl-4-ylmethyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.25h， 以99%的产率得到(4R,5S)-2,2,5-三甲基-1,3-二氧戊环-4-羧酸
  参考文献：
  名称：

  Scalable Synthesis of Enantiomerically Pure syn-2,3-Dihydroxybutyrate by Sharpless Asymmetric Dihydroxylation of p-Phenylbenzyl Crotonate

  摘要：

  An efficient four-step synthetic route to the useful chiral building block (2R,3S)-dihydroxybutyric acid acetonide in >95% ee is detailed. The sequence is readily scaled, requires no chromatography, and allows for efficient recycling of p-phenylbenzyl alcohol, an expedient for enantio- and diastereoenrichment by recrystallization.

  DOI：

  10.1021/jo2016746
• 作为产物：
  描述：

  p-phenylbenzyl crotonate 在 potassium osmate(VI) dihydrate 、 水 、 potassium carbonate 、 对甲苯磺酸 、 氢化奎宁(蒽醌-1,4-二基)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 叔丁醇 为溶剂， 反应 114.84h， 生成 biphenyl-4-ylmethyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate
  参考文献：
  名称：

  Scalable Synthesis of Enantiomerically Pure syn-2,3-Dihydroxybutyrate by Sharpless Asymmetric Dihydroxylation of p-Phenylbenzyl Crotonate

  摘要：

  An efficient four-step synthetic route to the useful chiral building block (2R,3S)-dihydroxybutyric acid acetonide in >95% ee is detailed. The sequence is readily scaled, requires no chromatography, and allows for efficient recycling of p-phenylbenzyl alcohol, an expedient for enantio- and diastereoenrichment by recrystallization.

  DOI：

  10.1021/jo2016746

文献信息

• Scalable Synthesis of Enantiomerically Pure <i>syn</i>-2,3-Dihydroxybutyrate by Sharpless Asymmetric Dihydroxylation of <i>p</i>-Phenylbenzyl Crotonate
  作者：Daniel J. Smaltz、Andrew G. Myers

  DOI：10.1021/jo2016746

  日期：2011.10.21

  An efficient four-step synthetic route to the useful chiral building block (2R,3S)-dihydroxybutyric acid acetonide in >95% ee is detailed. The sequence is readily scaled, requires no chromatography, and allows for efficient recycling of p-phenylbenzyl alcohol, an expedient for enantio- and diastereoenrichment by recrystallization.