hydroxy(phenyl)acetic acid (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl ester | 916525-81-0

• 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: hydroxy(phenyl)acetic acid (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl ester
• CAS: 916525-81-0
• 化学式: C₂₈H₃₂O₆
• 分子量: 464.558
• InChiKey: UANXWFANVNBIIP-GDRMZMBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  hydroxy(phenyl)acetic acid (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 (S)-(+)-扁桃酸 、 D-扁桃酸
  参考文献：
  名称：

  Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters

  摘要：

  Five partly novel aryl substituted m-hydrobenzoins were synthesized and the corresponding desymmetrized hydrobenzoin ethers evaluated as open chain chiral auxiliaries in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates, resulting in de values of up to 91%. Two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliary in the same type of reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.017
• 作为产物：
  描述：

  2,2'-dimethoxybenzoin 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 对甲苯磺酸一水合物 、 L-Selectride 、 sodium hydride 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 hydroxy(phenyl)acetic acid (1R,2S)-1,2-bis(2-methoxyphenyl)-2-(2-methylpropoxy)ethyl ester
  参考文献：
  名称：

  Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters

  摘要：

  Five partly novel aryl substituted m-hydrobenzoins were synthesized and the corresponding desymmetrized hydrobenzoin ethers evaluated as open chain chiral auxiliaries in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates, resulting in de values of up to 91%. Two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliary in the same type of reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.017