(S)(-)-Benzyl-2-Tosyloxypropionat | 70836-97-4

• 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: (S)(-)-Benzyl-2-Tosyloxypropionat
• 英文别名: benzyl (2S)-2-(4-methylphenyl)sulfonyloxypropanoate
• CAS: 70836-97-4
• 化学式: C₁₇H₁₈O₅S
• 分子量: 334.393
• InChiKey: VTIDIAIZOPXIFZ-AWEZNQCLSA-N

物化性质

• 沸点：
  473.4±33.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)(-)-Benzyl-2-Tosyloxypropionat 在 palladium on activated charcoal 氢气 作用下， 生成 (S)-2-(甲苯-4-磺酰氧基)-丙酸
  参考文献：
  名称：

  Synthesis of optically active .ALPHA.-alkyl or .ALPHA.-aryl acids from L-.ALPHA.-amino acids by the use of organocopper reagents.

  摘要：

  为了进一步探索L-α-氨基酸(I)在光学活性化合物合成中的用途，由I容易获得光学活性α-甲苯磺酰氧基酸及其衍生物(III)与几种类型的反应研究了有机铜试剂。尽管在形成不寻常的反应产物（如 β-酮酯 (dl-6) 和邻二醇 ((R)(+)-13））以及取代产物的产率较低方面仍然存在一些模糊性，但它已经很明显，当分别由L-苯丙氨酸、L-丙氨酸和L-亮氨酸制备的光学活性α-甲苯磺酰氧基酸用二烷基铜或二芳基铜酸锂处理时，取代反应可以几乎完全反转进行，得到相应的光学活性最大 α-烷基或 α-芳基酸收率63%。

  DOI：

  10.1248/cpb.27.747

文献信息

• Synthesis of a Peroxime Proliferator Activated Receptor (PPAR) α/γ Agonist via Stereocontrolled Williamson Ether Synthesis and Stereospecific S_N2 Reaction of <i>S</i>-2-Chloro Propionic Acid with Phenoxides
  作者：James A. Aikins、Michael Haurez、John R. Rizzo、Jean-Pierre Van Hoeck、Willy Brione、Jean-Paul Kestemont、Christophe Stevens、Xavier Lemair、Gregory A. Stephenson、Eric Marlot、Mindy Forst、Ioannis N. Houpis

  DOI：10.1021/jo050268e

  日期：2005.6.1

  The stereospecific synthesis of the PPAR alpha/gamma agonist I was accomplished via ethylation of the optically pure tribydroxy derivative 6, itself derived via an enzymatic resolution. The ethylation can be accomplished without epimerization only under strict control of the reaction conditions and the choice of base (sodium tert-amylate), temperature (-30 degrees C), order of addition, and solvent (DMF). The key diastereospecific S(N)2 reaction of the phenol 4 with S-2-chloropropionic acid is best achieved via the sodium phenoxide of 4 derived from Na-0 as the reagent of choice. The structure elucidation and key purification protocols to achieve pharmaceutical purity will also be described.
• Synthesis of optically active .ALPHA.-alkyl or .ALPHA.-aryl acids from L-.ALPHA.-amino acids by the use of organocopper reagents.
  作者：SHIRO TERASHIMA、CHUNGCHYI TSENG、KENJI KOGA

  DOI：10.1248/cpb.27.747

  日期：——

  With an aim to further explore the utility of L-α-amino acids (I) in the synthesis of optically active compounds, the reaction of optically active α-tosyloxy acids and their derivatives (III) readily obtainable from I, with several types of organocopper reagents were studied. Although there still remain some ambiguity in the formation of unusual reaction products such as the β-keto ester (dl-6) and the vicinal diol ((R)(+)-13) and in lower yields for the substitution products, it has become evident that when optically active α-tosyloxy acids prepared from L-phenylalanine, L-alanine, and L-leucine, respectively, are treated with lithium dialkyl- or diarylcuprates, the substitution reactions can proceed with almost full inversion to give corresponding optically active α-alkyl or α-aryl acids in max. 63% yield.

  为了进一步探索L-α-氨基酸(I)在光学活性化合物合成中的用途，由I容易获得光学活性α-甲苯磺酰氧基酸及其衍生物(III)与几种类型的反应研究了有机铜试剂。尽管在形成不寻常的反应产物（如 β-酮酯 (dl-6) 和邻二醇 ((R)(+)-13））以及取代产物的产率较低方面仍然存在一些模糊性，但它已经很明显，当分别由L-苯丙氨酸、L-丙氨酸和L-亮氨酸制备的光学活性α-甲苯磺酰氧基酸用二烷基铜或二芳基铜酸锂处理时，取代反应可以几乎完全反转进行，得到相应的光学活性最大 α-烷基或 α-芳基酸收率63%。