4-benzyloxy-3-hydroxy-2-methylpentanoic acid methyl ester | 94989-84-1

• 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: 4-benzyloxy-3-hydroxy-2-methylpentanoic acid methyl ester
• 英文别名: (2S,3S,4S)-4-benzyloxy-3-hydroxy-2-methyl-pentanoic acid methyl ester；methyl (2S,3S,4S)-3-hydroxy-2-methyl-4-phenylmethoxypentanoate
• CAS: 94989-84-1
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: HLRIYLMHWOOBBN-GVXVVHGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 (2S,3S,4S)-4-Benzyloxy-3-hydroxy-2-methyl-pentanoic acid 以 乙醚 为溶剂， 反应 0.5h， 生成 4-benzyloxy-3-hydroxy-2-methylpentanoic acid methyl ester
  参考文献：
  名称：

  Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes

  摘要：

  A chelation-controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of (S)-valinolderived ester with a variety of aldehydes proceeded with high syn-diastercoselectivities (up to 99:1) and isolated yields (94%). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01113-9

文献信息

• Synthesis of Propionate Motifs:  Diastereoselective Tandem Reactions Involving Anionic and Free Radical Based Processes
  作者：Yvan Guindon、Karine Houde、Michel Prévost、Benoit Cardinal-David、Serge R. Landry、Benoit Daoust、Mohammed Bencheqroun、Brigitte Guérin

  DOI：10.1021/ja010805m

  日期：2001.9.1

  employing a Mukaiyama reaction in tandem with a hydrogen transfer reaction for the elaboration of propionate motifs. The nature of the protecting groups on the chiral β-alkoxy aldehyde and the type of Lewis acid used are varied to modulate the stereochemical outcome of the tandem reactions. The mode of complexation is thus controlled (monodentate or chelate) for the Mukaiyama reaction to give access to

  本文报道了一种采用 Mukaiyama 反应与氢转移反应串联的策略，用于制作丙酸酯基序。手性 β-烷氧基醛上保护基团的性质和所用路易斯酸的类型各不相同，以调节串联反应的立体化学结果。因此，Mukaiyama 反应的络合模式受到控制（单齿或螯合），以提供合成或抗羟醛产物，自由基还原反应的前体。随后利用内环效应来控制氢转移步骤，从而可以实现顺式还原产物。以优异的产率和非对映选择性继续进行，所提出的合成序列可以访问syn-syn和syn-anti丙酸酯基序。
• Aldol-additions t0eα- and β-alkoxy aldehydes: The effect of chelation on simple diastereoselectivity
  作者：M.T. Reetz、K. Kesseler、A. Jung

  DOI：10.1016/s0040-4020(01)98807-6

  日期：——

  reaction of enol silanes with chiral α- and β-alkoxy aldehydes constitutes the only presently known, general way to perform aldol additions with chelation-control (asymmetric induction 90%). If the enol silane is prochiral, the additional stereoselection (simple diastereoselectivity) is surprisingly good. This unusual effect has been traced to syn-type of complexation of the aldehyde function.

  烯醇硅烷与手性α-和β-烷氧基醛的TiCl 4或SnCl 4介导的反应是目前唯一已知的通过螯合控制（不对称诱导率为90％）进行羟醛加成的一般方法。如果烯醇硅烷是手性的，则额外的立体选择（简单的非对映选择性）是令人惊讶的好。这种不寻常的作用可以追溯到醛官能团的络合同型。
• Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes
  作者：Arun K Ghosh、Jae-Hun Kim

  DOI：10.1016/s0040-4039(02)01113-9

  日期：2002.8

  A chelation-controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of (S)-valinolderived ester with a variety of aldehydes proceeded with high syn-diastercoselectivities (up to 99:1) and isolated yields (94%). (C) 2002 Elsevier Science Ltd. All rights reserved.