(S)-3-(4-苄氧基)-2-羟基-苯丙酸甲酯 | 481072-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (S)-3-(4-苄氧基)-2-羟基-苯丙酸甲酯
• 中文别名: (S)-3-(4-苄氧基苯基)-2-羟基丙酸甲酯；S-3-(4-苄氧基)-2-羟基-苯丙酸甲酯
• 英文名称: (S)-3-(p-benzyloxyphenyl)lactic acid methyl ester
• 英文别名: (S)-3-(4-Benzyloxy-phenyl)-2-hydroxy-propionic acid methyl ester；methyl (2S)-2-hydroxy-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 481072-37-1
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: LDEMOWMMKVQUEX-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-苄氧基)-2-羟基-苯丙酸甲酯 在 甲醇 、 lithium hydroxide monohydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.75h， 生成 (S)-2-(benzyloxy)-3-(4-(benzyloxy)phenyl)propanoic acid
  参考文献：
  名称：

  通过嗜氧性开放的Oxabicyclocyclo [2.2.1]庚烷进入铜绿素丝氨酸蛋白酶抑制剂：Microcin SF608的全合成。

  摘要：

  丝氨酸蛋白酶在许多生物学过程中起关键作用，并与多种人类疾病如血栓形成或癌症有关。在寻找丝氨酸蛋白酶的选择性抑制剂期间，在海洋蓝细菌中发现了一个名为铜绿菌素的线性肽家族。我们在本文中报道了进入这些天然产物的合成挑战性核心片段的进入途径。从常见的氧双环结构单元11开始，我们进入了铜绿素酶的八氢吲哚核心，以微素SF608的全合成为例（2）。合成策略的关键是高效生成草甘膦SF608的氢吲哚基序的氧杂双环[2.2.1]庚烷的亲核开环。此外，在合成过程中，我们观察到了异常的区域选择性环氧化物的减少。对该反应进行的详细实验研究使我们提出了一种机制原理，其中涉及通过氨基甲酸酯NH基团传递分子内氢原子以控制均相环氧化物裂解的区域选择性。

  DOI：

  10.1002/chem.201400046
• 作为产物：
  描述：

  3-(4-benzyloxyphenyl)-2-oxopropanoic acid 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 生成 (R)-3-(4-benzyloxy-phenyl)-2-hydroxy-propionic acid methyl ester 、 (S)-3-(4-苄氧基)-2-羟基-苯丙酸甲酯
  参考文献：
  名称：

  3-Aryl-2-oxo-propanoic 酸的对映选择性还原：酶促和过渡金属催化方法的比较

  摘要：

  苯乳酸是缩肽的重要成分，缩肽是一大类天然产物，具有广泛的生物活性。尽管有多种对映选择性合成 α-羟基酸的方法，但几乎没有研究可用于解决过渡金属和酶催化方法制备取代苯乳酸或更一般芳基乳酸的底物选择性。我们在此报告了 Rh-DiPAMP（DiPAMP = 1,2-乙二基双 [（邻甲氧基苯基）苯基膦]）和乳酸脱氢酶催化的几种 3-芳基-2-氧代丙酸的对映选择性还原的比较结果。

  DOI：

  10.1002/ejoc.201201506

文献信息

• Synthesis of Microcin SF608 through Nucleophilic Opening of an Oxabicyclo[2.2.1]heptane
  作者：Stefan Diethelm、Corinna S. Schindler、Erick M. Carreira

  DOI：10.1021/ol1017189

  日期：2010.9.3

  The total synthesis of Microcin SF608 is reported. Access to the octahydroindole core structure of Microcin SF608 relies on the TMSOTf/NEt3-mediated opening of an oxabicyclic ring system. Additional highlights of the synthetic strategy that is reported include a highly regioselective epoxide reduction and photolytic excision of a 3° alcohol.

  报道了Microcin SF608的全合成。Microcin SF608的八氢吲哚核心结构的获得依赖于TMSOTf / NEt 3介导的氧杂双环系统的打开。报道的合成策略的其他亮点包括高度区域选择性环氧化物的还原和3°醇的光解。
• 3-Aryl-A-oxy substituted propanoic acids and a process for their preparation
  申请人：——

  公开号：US20040248849A1

  公开（公告）日：2004-12-09

  The present invention relates to novel antidiabetic compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs and pharmaceutically acceptable compositions containing them. More particularly, the present invention relates to novel 3-aryl-&agr;-oxy substituted propanoic acids of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs and pharmaceutically acceptable compositions containing them. Formula (I) where R 1 represents t-butyldimethyl silyl, trimethyl silyl or alkoxyalkyl group; R 2 represents hydrogen or substituted or unsubstituted (C 1 -C 6 )alkyl group. 1

  本发明涉及新型抗糖尿病化合物及其衍生物、类似物、互变异构体、立体异构体、多晶形式和药学上可接受的含有它们的组合物。更具体地，本发明涉及一般式（I）的新型3-芳基-&agr;-氧基取代的丙酸类化合物，其衍生物、类似物、互变异构体、立体异构体、多晶形式和药学上可接受的含有它们的组合物。其中，式（I）中，R1表示叔丁基二甲基硅基、三甲基硅基或烷氧基烷基；R2表示氢或取代或未取代的（C1-C6）烷基。
• 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.
• [EN] 3-ARYL- DOLLAR G(a)-OXY SUBSTITUTED PROPANOIC ACIDS AND A PROCESS FOR THEIR PREPARATION<br/>[FR] ACIDES PROPANOIQUES SUBSTITUES PAR 3-ARYL- DOLLAR G(a)-OXY ET LEUR PROCEDE DE PREPARATION
  申请人：REDDY RESEARCH FOUNDATION

  公开号：WO2003002575A1

  公开（公告）日：2003-01-09

  The present invention relates to novel antidiabetic compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs and pharmaceutically acceptable compositions containing them. More particularly, the present invention relates to novel 3-aryl-α-oxy substituted propanoic acids of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs and pharmaceutically acceptable compositions containing them. Formula (I) where R1 represents t-butyldimethyl silyl, trimethyl silyl or alkoxyalkyl group; R2 represents hydrogen or substituted or unsubstituted (C¿1?-C6)alkyl group.
• [EN] NOVEL 3-ARYL-2-HYDROXY PROPANOL DERIVATIVES AND A PROCESS FOR THEIR PREPARATION<br/>[FR] NOUVEAUX DERIVES DE 3-ARYL-2-HYDROXY PROPANOL ET PROCEDE DE PREPARATION ASSOCIE
  申请人：REDDY RESEARCH FOUNDATION

  公开号：WO2003008362A1

  公开（公告）日：2003-01-30

  The present invention relates to novel antidiabetic compounds, their derivatives, their analogs, their polymorphs and pharmaceutically acceptable compositions containing them. More particularly, the present invention relates to novel 3-aryl-2-hydroxy propanol of general formula (I), their derivatives, their analogs, their polymorphs and pharmaceutically acceptable compositions containing them, wherein R?1 and R2¿ may be same or different and represent hydrogen or (C¿1?-C6)alkyl or OR?1 and OR2¿ together form a substituted or unsubstituted 5 membered cyclic structure containing carbon and oxygen atoms.