(R)-2-羟基-3-苯丙酸叔丁酯 | 111505-52-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (R)-2-羟基-3-苯丙酸叔丁酯
• 英文名称: (R)-tert-butyl 2-hydroxy-3-phenylpropanoate
• 英文别名: Tert-butyl (R)-2-hydroxy-3-phenylpropionate；tert-butyl (2R)-2-hydroxy-3-phenylpropanoate
• CAS: 111505-52-3
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: GMYNKCIZSNJVEE-LLVKDONJSA-N

物化性质

• 沸点：
  320.3±22.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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)-2-羟基-3-苯丙酸叔丁酯 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 以19%的产率得到D-3-苯乳酸
  参考文献：
  名称：

  Stereocontrolled synthesis of D-α-hydroxy carboxylic acid from L-amino acids

  摘要：

  DOI：

  10.1016/s0040-4039(00)95997-5
• 作为产物：
  描述：

  D-3-苯乳酸 在 4-二甲氨基吡啶 、 乙酰氯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 (R)-2-羟基-3-苯丙酸叔丁酯
  参考文献：
  名称：

  Serendipitous Discovery of α-Hydroxyalkyl Esters as β-Lactamase Substrates

  摘要：

  O-(1-Carboxy-1-alkyloxycarbonyl) hydroxamates were found to spontaneously decarboxylate in aqueous neutral buffer to form O-(2-hydroxyalkylcarbonyl) hydroxamates, While the former molecules do not react rapidly with serine beta-lactamases, the latter are quite good substrates of representative class A and C, but not D, enzymes, and particularly of a class C enzyme. The enzymes catalyze hydrolysis of these compounds to a mixture of the alpha-hydroxy acid and hydroxamate. Analogous compounds containing aryloxy leaving groups rather that hydroxamates are also substrates. Structure-activity experiments showed that the alpha-hydroxyl group was required for any substantial substrate activity. Although both D- and L-alpha-hydroxy acid derivatives were substrates, the former were preferred. The response of the class C activity to pH and to alternative nucleophiles (methanol and D-phenylalanine) suggested that the same active site functional groups participated in catalysis as for classical substrates. Molecular modeling was employed to explore how the alpha-hydroxy group might interact with the class C beta-lactamase active site. Incorporation of the alpha-hydroxyalkyl moiety into novel inhibitors will be of considerable interest.

  DOI：

  10.1021/bi101071r

文献信息

• Total Synthesis of the Antifungal Depsipeptide Petriellin A
  作者：Marianne M. Sleebs、Denis Scanlon、John Karas、Rani Maharani、Andrew B. Hughes

  DOI：10.1021/jo201017w

  日期：2011.8.19

  We report the solid-phase total synthesis of the antifungal highly modified cyclic depsipeptide petriellin A. The synthesis confirms earlier reports on the absolute configuration of the natural product. The solid-phase approach resulted in a protected linear precursor, which was cleaved from the solid support prior to cyclization and final deprotection. Use of advanced coupling agents for several hindered

  我们报告了抗真菌的高度修饰的环状depsipeptide petriellin A的固相全合成。该合成证实了关于天然产物的绝对构型的早期报道。固相方法得到受保护的线性前体，其在环化和最终脱保护之前从固体支持物上裂解下来。先进的偶联剂用于几种受阻酰胺是合成的一个特征。天然产物的总产率为5％。
• First total synthesis of cyclodepsipeptides clavatustide A and B and their enantiomers
  作者：Suresh Kumar Chettu、Rajesh Bagepalli Madhu、Gajendrasinh Balvantsinh Raolji、Korupolu Raghu Babu、N. S. Kameswara Rao、Srividya Gopalakrishnan、Ayesha Ismail、G. Bhanuprakash Reddy、Syed Shafi

  DOI：10.1039/c6ra08861a

  日期：——

  The enantiopure synthesis of clavatustides A (1) and B (3) were accomplished by a seven step synthetic protocol starting from commercially available (R)-phenyllactic acid. As the optical rotation values of synthetic (R)-clavatustides A and B were not in agreement with the reported values, the corresponding antipodes 2 and 4 were synthesized from (S)-phenyllactic acid to address the issue. Both (R)

  通过从市售（R）-苯基乳酸开始的七步合成规程完成对甲壳甾类化合物A（1）和B（3）的对映纯合成。由于合成的（R）-蛤壳类杀虫剂A和B的旋光度值与报告的值不一致，因此从（S）-苯基乳酸合成了相应的对映体2和4来解决该问题。（R）和（S）使用MTT分析法评估了甲壳类固醇A和B对三种人类癌细胞系的抗增殖活性。发现子宫颈癌细胞系（HeLa）在降低细胞活力方面对测试化合物最敏感。与它们的对映异构体（R-异构体）相比，S-异构体（2和4）对HeLa细胞系的IC 50分别为24.5和26.8μM ，表现出更好的抗增殖活性。所有测试的化合物对正常肺细胞的细胞活力影响很小，表明这些化合物对正常细胞无毒。
• 3-Pyrroline-1-carbonyl (Pyroc) Group: A Removable Protecting Group for the Kinetic Resolution of Racemic Carboxylic Acids and Alcohols through Catalytic Asymmetric Acylation
  作者：Kazuaki Ishihara、Akira Sakakura、Shuhei Umemura

  DOI：10.1055/s-0029-1217321

  日期：——

  The O-3-pyrroline-1-carbonyl (O-Pyroc) group and 3-pyrrolinamide are useful removable protecting groups for the kinetic resolution of racemic α-hydroxycarboxylic acids, β-hydroxycarboxylic acids, 1,2-dicarboxylic acids, and 1,2-diols using the L -histidine-derived bifunctional catalysts. The Pyroc group can be easily introduced from Pyroc chloride. Selective deprotection of the Pyroc group and 3-pyrrolinamide

  O-3-吡咯啉-1-羰基 (O-Pyroc) 基团和 3-吡咯啉酰胺是有用的可去除保护基团，可用于外消旋 α-羟基羧酸、β-羟基羧酸、1,2-二羧酸和 1 ,2-二醇使用 L-组氨酸衍生的双功能催化剂。Pyroc 基团可以很容易地从 Pyroc 氯化物引入。Pyroc 基团和 3-吡咯啉酰胺的选择性脱保护可以通过 DDQ 氧化进行，然后使用氢氧化钠水解，无需差向异构化。
• Ring opening of benzoxazinones: An improved and efficient synthesis of clavatustides A & B
  作者：Suresh Kumar Chettu、Lakshmi Narayana Sharma Konidena、Raghu Babu Korupolu、N.S. Kameswara Rao、Raju Doddipalla、Hima Bindu Gandham、Ramakrishna Guduru

  DOI：10.1016/j.tetlet.2017.07.059

  日期：2017.8

  Ag2O mediated esterification of (R)-tert-butyl 2-hydroxy-3-phenylpropanoate has been realized via the effective ring opening of benzoxazinones that resulted in the efficient synthesis of cyclodepsipeptides clavatustides A and B and their enantiomers in very good overall yields.

  已通过苯并恶嗪酮的有效开环实现了Ag 2 O介导的（R）-叔丁基-2-羟基-3-苯基丙酸酯的酯化反应，从而有效地合成了环二肽Clavatustides A和B及其对映异构体，并且收率很高。 。
• Synthesis of phenyl substituted valinomycins
  作者：Yves L. Dory、John M. Mellor、Jerome E. McAleer

  DOI：10.1016/0040-4020(95)00964-7

  日期：1996.1

  The synthesis is described of a modified valmomycin, which incorporates phenyl groups located around the exterior belt. The synthesis is accomplished by a build up of linear fragments using both dicyclohexylcarbodamide and pentafluoroester methods of coupling. The final cyclisation is accomplished using the pentafluoroester protocol. The modified valinomycin is shown to be an effective ligand for complexation

  描述了修饰的伐木霉素的合成，该伐木霉素结合了位于外部传送带周围的苯基。合成是通过使用二环己基碳酰胺和五氟酯的偶联方法建立线性片段来完成的。最后的环化反应是使用五氟酯方案完成的。修饰的缬霉素被证明是与钾离子络合的有效配体。核磁共振和电化学研究均表明，修饰的缬霉素具有与母缬霉素相似的性质，因此外围的苯基取代不会破坏氢键的网络，而氢键的网络会影响缬霉素的构象。