(R)-methyl 2-(hydroxymethyl)butanoate | 72604-81-0

• 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: (R)-methyl 2-(hydroxymethyl)butanoate
• 英文别名: methyl (R)-2-(hydroxymethyl)butanoate；2-hydroxymethyl-butyric acid methyl ester；methyl (2R)-2-(hydroxymethyl)butanoate
• CAS: 72604-81-0
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: AICAOTFMUITLFU-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-(hydroxymethyl)butanoate 在 咪唑 、 二异丁基氢化铝 作用下， 生成 (-)-(2S)-2-((tert-Butyldimethylsiloxy)methyl)butan-1-ol
  参考文献：
  名称：

  Discovery of para-alkylthiophenoxyacetic acids as a novel series of potent and selective PPARδ agonists

  摘要：

  A novel series of potent and selective PPAR delta agonists, para-alkylthiophenoxyacetic acids, was identified. The synthesis and structure-activity relationships are described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.007
• 作为产物：
  描述：

  (R)-2-(acetoxymethyl)butanoic acid 在 potassium carbonate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 生成 (R)-methyl 2-(hydroxymethyl)butanoate
  参考文献：
  名称：

  蜘蛛致病性真菌代谢产物托鲁比隆D的四种立体异构体的合成及抑菌活性

  摘要：

  蜘蛛致病性真菌代谢产物托瑞比隆D的四种立体异构体以1-酪氨酸或d-酪氨酸为起始原料，首次以10％的总收率合成。3-癸三烯酰基侧链通过（E）-选择性HWE和Wittig烯化反应组装并连接。它们对药物敏感的大肠杆菌菌株的抗生素活性差异很大。

  DOI：

  10.1021/acs.orglett.6b00245

文献信息

• Synthesis of Enantiomerically Enriched 2-Hydroxymethylalkanoic Acids by Oxidative Desymmetrisation of Achiral 1,3-Diols Mediated by<i>Acetobacter aceti</i>
  作者：Elisabetta Brenna、Flavia Cannavale、Michele Crotti、Valerio De Vitis、Francesco G. Gatti、Gaia Migliazza、Francesco Molinari、Fabio Parmeggiani、Diego Romano、Sara Santangelo

  DOI：10.1002/cctc.201601051

  日期：2016.12.19

  achiral 2‐alkyl‐1,3‐diols is performed by oxidation of one of the two enantiotopic primary alcohol moieties by means of Acetobacter aceti MIM 2000/28 to afford the corresponding chiral 2‐hydroxymethyl alkanoic acids (up to 94 % ee). The procedure, carried out in aqueous medium under mild conditions of pH, temperature and pressure, contributes to enlarge the portfolio of enzymatic oxidations available

  非手性2-烷基-1,3-二醇的立体选择性去对称化是通过醋乙酸醋杆菌MIM 2000/28氧化两个对位伯醇部分之一进行的，以提供相应的手性2-羟甲基链烷酸（最高94 ％ee）。该过程在pH，温度和压力中等的水性介质中进行，有助于扩大有机化学家可用于开发可持续生产工艺的酶促氧化反应的范围。
• 4-(PHENOXYALKYL)THIO)-PHENOXYACETIC ACIDS AND ANALOGS
  申请人：Janssen Pharmaceutica NV

  公开号：US20160199342A1

  公开（公告）日：2016-07-14

  The invention features 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs, compositions containing them, and methods of using them as PPAR delta modulators to treat or inhibit the progression of, for example, dyslipidemia.

  这项发明涉及4-((苯氧烷基)硫基)-苯氧乙酸及其类似物、包含它们的组合物，以及使用它们作为PPARδ调节剂的方法，用于治疗或抑制例如脂质代谢异常等疾病的进展。
• 4-((Phenoxyalkyl)thio)-phenoxyacetic acids and analogs
  申请人：Janssen Pharmaceutica N.V.

  公开号：EP2100877A1

  公开（公告）日：2009-09-16

  The invention features 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs, compositions containing them, and their use as PPAR delta modulators to treat or inhibit the progression of, for example, dyslipidemia.

  本发明的特点是 4-((苯氧基烷基)硫基)-苯氧基乙酸及其类似物、含有它们的组合物，以及它们作为 PPAR delta 调节剂用于治疗或抑制血脂异常等疾病的进展。
• [EN] 4-((PHENOXYALKYL)THIO)-PHENOXYACETIC ACIDS AND ANALOGS<br/>[FR] ACIDES 4-((PHENOXYALKYL)THIO)-PHENOXYACETIQUES ET ANALOGUES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005042478A3

  公开（公告）日：2005-07-21
• Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C
  作者：Henning J. Jessen、Andreas Schumacher、Fabian Schmid、Andreas Pfaltz、Karl Gademann

  DOI：10.1021/ol201692h

  日期：2011.8.19

  Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation In high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrublelione C, which led to the assignment of the configuration of the natural product as (R).