(2R,3R,4R,5R)-2-(hydroxymethyl)-5-(4-methoxyphenyl)pyrrolidine-3,4-diol | 223595-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,3R,4R,5R)-2-(hydroxymethyl)-5-(4-methoxyphenyl)pyrrolidine-3,4-diol
• CAS: 223595-43-5
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: MMPIADOYZHTWHM-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (2R,3R,4R,5R)-2-(hydroxymethyl)-5-(4-methoxyphenyl)pyrrolidine-3,4-diol 在 palladium dihydroxide 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 以84%的产率得到(2R,3R,4R,5R)-2-(hydroxymethyl)-5-(4-methoxyphenyl)-1-methylpyrrolidine-3,4-diol
  参考文献：
  名称：

  Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library

  摘要：

  Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A ( 20) and B ( 18) against alpha-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 mu M, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.063
• 作为产物：
  描述：

  L-焦谷氨酸 在 palladium diacetate 甲酸 、 2,6-二叔丁基-4-甲基吡啶 、 硫酸 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 74.0h， 生成 (2R,3R,4R,5R)-2-(hydroxymethyl)-5-(4-methoxyphenyl)pyrrolidine-3,4-diol
  参考文献：
  名称：

  内环烯氨基甲酸酯与重氮盐的Heck反应。（-）-codonopsine和（-）-codonopsinine生物碱的形式对映选择性合成，以及新的C-芳基氮杂糖的合成

  摘要：

  吡咯烷生物碱（-）-codonopsine和（-）-codonopsinine的形式总合成以及新的C-芳基氮杂糖的合成是由一种常见的5元对映体纯的内环烯氨基甲酸酯完成的。这些合成过程中的关键步骤依赖于Heck反应的一种新颖实用的形式，该反应涉及到内环烯氨基甲酸酯和重氮盐。

  DOI：

  10.1016/s0040-4039(99)00151-3

文献信息

• Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation
  作者：Lukáš Ďurina、Anna Ďurinová、František Trejtnar、Ľuboš Janotka、Lucia Messingerová、Jana Doháňošová、Ján Moncol、Róbert Fischer

  DOI：10.3762/bjoc.17.188

  日期：——

  intermediate, and the substrate-directed epoxidation of the terminal double bond of the corresponding γ-amino-α,β-diol with aqueous hydrogen peroxide catalyzed by phosphotungstic heteropoly acid. Each of the key reactions proceeded with an excellent diastereoselectivity (dr > 95:5). (±)-Codonopsinol B was prepared in 10 steps with overall 8.4% yield. The antiproliferative effect of (±)-codonopsinol B

  提出了一种从非手性材料出发，高度非对映选择性合成多羟基化吡咯烷生物碱 (±)-党参醇 B 及其N-正甲基类似物的方法。该策略依赖于2,3-二氢异恶唑与原位生成的DMDO的反式立体选择性环氧化，乙烯基-MgBr/CeCl 3的顺式选择性α-螯合控制加成到异恶唑烷-4,5-二醇中间体中，磷钨杂多酸催化过氧化氢水溶液对相应的γ-氨基-α,β-二醇的末端双键进行底物定向环氧化。每个关键反应均以优异的非对映选择性进行（dr > 95:5）。 (±)-党参醇 B 分 10 个步骤制备，总产率为 8.4%。使用多种细胞系模型评估了 (±)-党参酚 B 及其N-正甲基类似物的抗增殖作用。
• Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library
  作者：En-Lun Tsou、Sih-Yu Chen、Ming-Hsun Yang、Shih-Chi Wang、Ting-Ren Rachel Cheng、Wei-Chieh Cheng

  DOI：10.1016/j.bmc.2008.10.063

  日期：2008.12.15

  Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A ( 20) and B ( 18) against alpha-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 mu M, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases. (C) 2008 Elsevier Ltd. All rights reserved.
• Heck reaction of endocyclic enecarbamates with diazonium salts. Formal enantioselective syntheses of alkaloids (−)-codonopsine and (−)-codonopsinine, and the synthesis of a new C-aryl azasugar
  作者：Denilson F. Oliveira、Elias A. Severino、Carlos Roque D. Correia

  DOI：10.1016/s0040-4039(99)00151-3

  日期：1999.3

  Formal total syntheses of the pyrrolidine alkaloids (−)-codonopsine and (−)-codonopsinine, as well as the synthesis of a new C-aryl azasugar were accomplished from a common 5-membered, enantiomerically pure endocyclic enecarbamate. The key step in those syntheses relies on a novel and practical version of the Heck reaction involving endocyclic enecarbamates and diazonium salts.

  吡咯烷生物碱（-）-codonopsine和（-）-codonopsinine的形式总合成以及新的C-芳基氮杂糖的合成是由一种常见的5元对映体纯的内环烯氨基甲酸酯完成的。这些合成过程中的关键步骤依赖于Heck反应的一种新颖实用的形式，该反应涉及到内环烯氨基甲酸酯和重氮盐。