(S)-2-acetoxy-3-(4-(benzyloxy)phenyl)propanoic acid | 267228-34-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-2-acetoxy-3-(4-(benzyloxy)phenyl)propanoic acid
• 英文别名: (I+/-S)-I+/--(Acetyloxy)-4-(phenylmethoxy)benzenepropanoic acid；(2S)-2-acetyloxy-3-(4-phenylmethoxyphenyl)propanoic acid
• CAS: 267228-34-2
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: RPQMOXWARPYEDJ-KRWDZBQOSA-N

物化性质

• 熔点：
  99-101 °C(Solv: water (7732-18-5))
• 沸点：
  490.1±40.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-acetoxy-3-(4-(benzyloxy)phenyl)propanoic acid 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (S)-3-(4-苄氧基苯基)-2-羟基丙酸
  参考文献：
  名称：

  N-（α-羟酰基）-甘氨酸酯通过钯催化的烯丙基烷基化的立体选择性改性

  摘要：

  N-（α-羟基酰基）-甘氨酸酯可以用作Pd催化的烯丙基烷基化反应中的优良亲核试剂。该方法允许立体选择引入各种侧链，包括高度官能化的侧链。两种非对映异构体均可通过改变反应条件来获得。此外，使用甲锡烷基化碳酸酯会引入乙烯基锡烷基序，这些基序可用于后续的C–C偶联反应。

  DOI：

  10.1021/acs.orglett.9b01497
• 作为产物：
  描述：

  L-酪氨酸 在 copper(ll) sulfate pentahydrate 、 溶剂黄146 、 sodium hydroxide 、 亚硝酸异戊酯 作用下， 以 水 为溶剂， 反应 73.0h， 生成 (S)-2-acetoxy-3-(4-(benzyloxy)phenyl)propanoic acid
  参考文献：
  名称：

  N-（α-羟酰基）-甘氨酸酯通过钯催化的烯丙基烷基化的立体选择性改性

  摘要：

  N-（α-羟基酰基）-甘氨酸酯可以用作Pd催化的烯丙基烷基化反应中的优良亲核试剂。该方法允许立体选择引入各种侧链，包括高度官能化的侧链。两种非对映异构体均可通过改变反应条件来获得。此外，使用甲锡烷基化碳酸酯会引入乙烯基锡烷基序，这些基序可用于后续的C–C偶联反应。

  DOI：

  10.1021/acs.orglett.9b01497

文献信息

• Total Synthesis and Structural Revision of Aeruginosin KT608A
  作者：Manuel Scherer、Karl Gademann

  DOI：10.1021/acs.orglett.7b01822

  日期：2017.7.21

  The synthesis of the presumed structure of aeruginosin KT608A was accomplished for the first time. The unusual d-diepi-Choi core was prepared from tyrosine via C–H activation and heterogeneous hydrogenation. Due to differences in the spectral data of synthetic and natural samples, a revised structure featuring l-diepi-Choi was proposed, which was synthesized and confirmed to be identical. On the basis

  铜绿素菌素KT608A的假定结构的合成是第一次完成。酪氨酸通过C–H活化和非均相加氢制得了不寻常的d - dipipi -Choi核。由于在合成的和天然的样品，经修订的结构特征的频谱数据的差异升- diepi -Choi提出，将其合成并确认为相同的。基于这些发现，提出了另外六种铜绿素酶（KT608B，KT650，GH553，DA495A，DA511和KB676）的修订结构。
• Process for the preparation of new antidiabetic agents
  申请人：DR. REDDY'S LABORATORIES LIMITED

  公开号：US20030125553A1

  公开（公告）日：2003-07-03

  The present invention relates to an improved process for the preparation of novel antidiabetic compounds having formula (1) where R 1 represents hydrogen or lower alkyl group and X represents hydrogen or halogen atom. 1

  本发明涉及一种改进的制备新型抗糖尿病化合物的方法，其化学式为（1），其中R1代表氢或较低的烷基团，X代表氢或卤素原子。
• 4,4-Dimethyl-1,2,3,4-tetrahydroquinoline-based PPARα/γ agonists. Part I: Synthesis and pharmacological evaluation
  作者：Cécile Parmenon、Jérôme Guillard、Daniel-Henri Caignard、Nathalie Hennuyer、Bart Staels、Valérie Audinot-Bouchez、Jean-Albert Boutin、Catherine Dacquet、Alain Ktorza、Marie-Claude Viaud-Massuard

  DOI：10.1016/j.bmcl.2008.01.067

  日期：2008.3

  Type-2 diabetes (T2D) is a complex metabolic disease characterized by insulin resistance in the liver and peripheral tissues accompanied by a defect in pancreatic beta-cell. Since their discovery three subtypes of Peroxisomes Proliferators Activated Receptors were identified namely PPAR alpha, PPAR gamma and PPAR beta/(delta). We were interested in designing novel PPAR gamma selective agonists and/or dual PPAR alpha/gamma agonists. Based on the typical topology of synthetic PPAR agonists, we focused our design approach on 4,4-dimethyl-1,2,3,4-tetrahydroquinoline as novel cyclic tail. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Microcin SF608
  作者：Nativitat Valls、Mercè Vallribera、Meritxell López-Canet、Josep Bonjoch

  DOI：10.1021/jo025709y

  日期：2002.7.1

  The first total synthesis of aquatic peptide microcin SF608 is described. Coupling of L-Hpla with the dipeptide L-Phe-L-Choi followed by coupling with agmatine and a deprotection step gave microcin SF608. In addition, the levorotatory character of L-Hpla (5) was thoroughly established, and the conformational analysis of L-Choi containing peptides 1 and 8-10 was performed using NMR spectroscopy to examine the cis-trans isomer equilibrium of the L-Phe-L-Choi amide bond.
• Syntheses of Both the Putative and Revised Structures of Aeruginosin EI461 Bearing a New Bicyclic α-Amino Acid
  作者：Nativitat Valls、Mercè Vallribera、Shmuel Carmeli、Josep Bonjoch

  DOI：10.1021/ol0273250

  日期：2003.2.1

  [GRAPHICS]The putative structure of the naturally occurring aquatic peptide aeruginosin EI461 has been prepared from D-tyrosine. A corrected structure for aeruginosin EI461 is proposed, and the structure is proven by synthesis, which was accomplished using the new alpha-amino acid (2S,-3aR,6R,7aR)-6-hydroxy-2-carboxyoctahydroindole, prepared from L-tyrosine. Succesive couplings of the dipeptide D-Leu-3a,7a-diepi-L-Choi with L-Hpla and NH4OH and a deprotection step gave aeruginosin EI461.