oxophenylacetic acid (1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethyl ester | 866457-10-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: oxophenylacetic acid (1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethyl ester
• 英文别名: [(1R,2S)-2-[(2-methylpropan-2-yl)oxy]-1,2-diphenylethyl] 2-oxo-2-phenylacetate
• CAS: 866457-10-5
• 化学式: C₂₆H₂₆O₄
• 分子量: 402.49
• InChiKey: GZJVRYNWGDHRMK-RPWUZVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  oxophenylacetic acid (1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethyl ester 在 L-Selectride 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-hydroxyphenylacetic acid (1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethyl ester 、 (S)-hydroxyphenylacetic acid (1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethyl ester
  参考文献：
  名称：

  Synthesis of novel chiral hydrobenzoin mono-tert-butyl ethers derived from m-hydrobenzoin and their application as chiral auxiliaries in the diastereoselective reduction of α-keto esters

  摘要：

  Three m-hydroberizoin derived chiral hydrobenzoin mono-tert-butyl ethers were synthesized by a new, reaction pathway and tested as chiral auxiliaries in the L-selectride (R) mediated stereoselective reduction of their corresponding phellyl glyoxylates. As a result, improved stereoselectivities of up to a ratio of 92:8 compared to 84:16 with the initially examined analogous benzyl ether were achieved. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.033
• 作为产物：
  描述：

  [2S-(2α(1S*,2R*),3aα,4β,7β,7aα)]-[2-(1,1-dimethylethoxy)-1,2-diphenylethoxy]octahydro-7,8,8-trimethyl-4,7-methanobenzofuran 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 oxophenylacetic acid (1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethyl ester
  参考文献：
  名称：

  Synthesis of novel chiral hydrobenzoin mono-tert-butyl ethers derived from m-hydrobenzoin and their application as chiral auxiliaries in the diastereoselective reduction of α-keto esters

  摘要：

  Three m-hydroberizoin derived chiral hydrobenzoin mono-tert-butyl ethers were synthesized by a new, reaction pathway and tested as chiral auxiliaries in the L-selectride (R) mediated stereoselective reduction of their corresponding phellyl glyoxylates. As a result, improved stereoselectivities of up to a ratio of 92:8 compared to 84:16 with the initially examined analogous benzyl ether were achieved. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.033

文献信息

• Chiral linker. Part 4: Diastereoselective addition of RZnX to α-keto esters using m-hydrobenzoin derived chiral auxiliaries in solution and on solid support and their application in the stereoselective synthesis of frontalin
  作者：Christian Schuster、Max Knollmueller、Peter Gaertner

  DOI：10.1016/j.tetasy.2006.08.016

  日期：2006.9

  Two recently reported, m-hydrobenzoin derived open chain chiral auxiliaries, which were developed for application in either solution or immobilized on a solid support, were tested in the diastereoselective addition of RZnX to their corresponding phenylglyoxylates and pyruvates, respectively, resulting in diastereoisomeric excesses of up to > 98% de. The optimized procedure was applied in the stereoselective synthesis of frontalin, the aggregation pheromone of pine bark beetles of the Dendroctonus family, by the use of both the solution phase and the polymer supported chiral auxiliary. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of novel chiral hydrobenzoin mono-tert-butyl ethers derived from m-hydrobenzoin and their application as chiral auxiliaries in the diastereoselective reduction of α-keto esters
  作者：Christian Schuster、Joachim Broeker、Max Knollmueller、Peter Gaertner

  DOI：10.1016/j.tetasy.2005.06.033

  日期：2005.8

  Three m-hydroberizoin derived chiral hydrobenzoin mono-tert-butyl ethers were synthesized by a new, reaction pathway and tested as chiral auxiliaries in the L-selectride (R) mediated stereoselective reduction of their corresponding phellyl glyoxylates. As a result, improved stereoselectivities of up to a ratio of 92:8 compared to 84:16 with the initially examined analogous benzyl ether were achieved. (c) 2005 Elsevier Ltd. All rights reserved.