(2R,3R)-2-methyl-3-hydroxyhexanoic acid | 109106-14-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2R,3R)-2-methyl-3-hydroxyhexanoic acid
• 英文别名: (2R,3R)-3-hydroxy-2-methylhexanoic acid
• CAS: 109106-14-1
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: UBEKFGMRKUQZGX-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2R,3R)-2-methyl-3-hydroxyhexanoic acid 以 乙醚 为溶剂， 生成 (-)-threo-methyl 2-methyl-3-hydroxyhexanate
  参考文献：
  名称：

  对映体纯的抗羟醛缩醛的合成：高度立体选择性酯衍生的烯醇钛酸羟醛缩醛反应。

  摘要：

  DOI：

  10.1021/ja9539148
• 作为产物：
  描述：

  [(1R,2S)-2-[methyl(1,2,3,4,5,6,7,8-octahydroanthracen-9-ylsulfonyl)amino]-1-phenylpropyl] (2R,3R)-3-hydroxy-2-methylhexanoate 生成 (2R,3R)-2-methyl-3-hydroxyhexanoic acid
  参考文献：
  名称：

  的程度顺式-选择性为羧酸酯的硼介导的不对称醛醇缩合反应

  摘要：

  为顺式选择性羟醛缩合反应的新的手性试剂已经被开发了基于最近的发现，即羧酸酯的硼介导的醛醇缩合反应的立体化学通过该酯的醇部分的膨松度的控制，通过适当选择试剂，并受烯醇化条件的影响。这种易于获得的廉价试剂已被用于大环内酯单萜内酯的合成研究中。

  DOI：

  10.1016/s0040-4039(98)00123-3

文献信息

• Asymmetric and ?anti?-Selective Aldolisations of Acetates and Propionates. Preliminary Communication
  作者：Wolfgang Oppolzer、Jos� Marco-Contelles

  DOI：10.1002/hlca.19860690725

  日期：1986.10.29

  Starting from acetates 1 and propionates 6, TiCl4-mediated addition of their silyketene acetals 2 and 7 to aldehydes gave aldols 4 and 9, respectively, with high π-face and ‘anti’ differentiation (Schemes, and Tables 1 and 2). Alternation of the (E/Z)-enolate geometry led to reversed α- and β-inductions (7 9b, 8 10b). Non-destructive removal of the auxiliary yielded enantiomerically pure β -hydroxycarboxylic

  从乙酸盐1和丙酸酯6开始，TiCl 4介导的将它们的硅酮烯醇缩醛2和7加到醛中，分别得到具有高π面和'抗'区分性的醇醛4和9（方案，以及表1和表2）。（E / Z）烯醇几何形状的交替导致相反的α和β诱导（7 9b，8 10b）。非破坏性去除辅助生成的对映体纯的β-羟基羧酸13 。
• Employing Modular Polyketide Synthase Ketoreductases as Biocatalysts in the Preparative Chemoenzymatic Syntheses of Diketide Chiral Building Blocks
  作者：Shawn K. Piasecki、Clint A. Taylor、Joshua F. Detelich、June Liu、Jianting Zheng、Arkady Komsoukaniants、Dionicio R. Siegel、Adrian T. Keatinge-Clay

  DOI：10.1016/j.chembiol.2011.07.021

  日期：2011.10

  Chiral building blocks are valuable intermediates in the syntheses of natural products and pharmaceuticals. A scalable chemoenzymatic route to chiral diketides has been developed that includes the general synthesis of α-substituted, β-ketoacyl N-acetylcysteamine thioesters followed by a biocatalytic cycle in which a glucose-fueled NADPH-regeneration system drives reductions catalyzed by isolated modular

  手性构件是天然产物和药物合成中的有价值的中间体。已开发出一种可扩展的手性二酮化学反应路线，包括一般合成α-取代的β-酮酰基N-乙酰半胱胺硫酯，然后进行生物催化循环，其中葡萄糖驱动的NADPH再生系统驱动由分离的模块化聚酮合酶催化的还原反应（PKS）酮还原酶（KRs）。为了鉴定起活性，立体定向生物催化剂作用的KR，将11个分离的KR与5个二酮化合物一起孵育，并通过手性色谱法分析其产物。天然还原小的聚酮化合物中间体的KR对双酮化合物面板最为活跃，且立体定向性最高。扩大了几种生物催化反应的规模，以生产超过100毫克的产品。
• A General, Highly Anti-Stereoselective Aldolization Method via Camphor-Derived Boryl Enolates
  作者：Ying-Chuan Wang、An-Wei Hung、Chii-Shin Chang、Tu-Hsin Yan

  DOI：10.1021/jo9520147

  日期：1996.1.1

  Camphor-derived chiral boryl enolates are highly reactive and highly anti-stereoselective enolate synthon systems in aldol addition reactions promoted by a TiCl4 or SnCl4 cocatalyst. More significantly, this high-yield reaction exhibits remarkable generality with respect to the aldehyde nature, as illustrated by the rapid and anti-stereoselective aldolizations with the simple saturated and unsaturated aliphatic aldehydes, and aromatic aldehydes at temperatures as low as -90 degrees C. The enhanced reaction generality and anti stereoselectivity of camphor-derived boryl enolates suggests the importance of the nature of chiral auxiliary architecture in determining the aldol bond construction process. Final nondestructive camphor-based auxiliary removal via hydroperoxide-mediated hydrolysis affords enantiomerically pure anti-beta-hydroxy-alpha-methyl aldol products.
• OPPOLZER W.; MARCO-CONTELLES J., HELV. CHIM. ACTA, 69,(1986) N 7, 1699-1703
  作者：OPPOLZER W.、 MARCO-CONTELLES J.

  DOI：——

  日期：——
• Attainment of syn-selectivity for boron-mediated asymmetric aldol reactions of carboxylic esters
  作者：Ji-Feng Liu、Atsushi Abiko、Zhonghua Pei、Dana C Buske、Satoru Masamune

  DOI：10.1016/s0040-4039(98)00123-3

  日期：1998.4

  reagent for syn-selective aldol reactions has been developed based on the recent finding that the stereochemistry of the boron-mediated aldol reaction of a carboxylic ester is controlled by the bulkiness of the alcohol moiety of the ester, by the proper choice of reagents, and by the enolization conditions. This readily available, inexpensive reagent has been utilized in studies directed towards the synthesis

  为顺式选择性羟醛缩合反应的新的手性试剂已经被开发了基于最近的发现，即羧酸酯的硼介导的醛醇缩合反应的立体化学通过该酯的醇部分的膨松度的控制，通过适当选择试剂，并受烯醇化条件的影响。这种易于获得的廉价试剂已被用于大环内酯单萜内酯的合成研究中。