(2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol | 1101869-66-2

• 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-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol
• 英文别名: (-)-codonopsinol
• CAS: 1101869-66-2
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: VGEPCNNJGKDQTM-ICGCDAGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  82.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3R,4R,5R)-2-(benzyloxymethyl)-5-(3,4-dimethoxyphenyl)-1-methylpyrrolidine-3,4-diol 在 氢气 、 palladium dichloride 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以85%的产率得到(2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-5-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol
  参考文献：
  名称：

  Total synthesis of (−)-codonopsinol and (+)-2-epi codonopsinol via acid catalyzed amido cyclisation

  摘要：

  A short and stereoselective synthesis of (-)-codonopsinol 5 mid its C-2 epimer 6 were accomplished from, commercially available starting material D-1,5-gluconolactone, using acid mediated amido cyclisation as the key step The inhibitory activity of these compounds against. glucosidase and galactosidase has been studied (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2009.12.035

文献信息

• DDQ-Promoted Benzylic/Allylic sp³ C–H Activation for the Stereoselective Intramolecular C–N Bond Formation: Applications to the Total Synthesis of (−)-Codonopsinine, (+)-5-<i>epi</i>-Codonopsinine, (+)-Radicamine B, and (−)-Codonopsinol
  作者：Macha Lingamurthy、Yerri Jagadeesh、Katakam Ramakrishna、Batchu Venkateswara Rao

  DOI：10.1021/acs.joc.5b02275

  日期：2016.2.19

  This is the first report on an intramolecular C–N bond formation of an amide-tethered benzylic/allylic system using DDQ under neutral conditions which has been successfully applied to the total synthesis of naturally occurring pyrolidine alkaloids. The key steps for the synthesis of corresponding precursors involve Julia–Kociensky olefination/cross-metathesis and dihydroxylation reactions, and this

  这是关于在中性条件下使用DDQ的酰胺束缚的苄基/烯丙基系统的分子内C–N键形成的首次报道，该技术已成功应用于天然存在的吡咯烷生物碱的全合成。合成相应前体的关键步骤涉及Julia-Kociensky烯烃化/交叉复分解和二羟基化反应，并且该方法学还扩展到ω-不饱和N-磺酰胺提供哌啶。
• 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.
• Total synthesis of (−)-codonopsinol and (+)-2-epi codonopsinol via acid catalyzed amido cyclisation
  作者：Y. Jagadeesh、J. Santhosh Reddy、B. Venkateswara Rao、J. Lakshmi Swarnalatha

  DOI：10.1016/j.tet.2009.12.035

  日期：2010.2

  A short and stereoselective synthesis of (-)-codonopsinol 5 mid its C-2 epimer 6 were accomplished from, commercially available starting material D-1,5-gluconolactone, using acid mediated amido cyclisation as the key step The inhibitory activity of these compounds against. glucosidase and galactosidase has been studied (C) 2009 Elsevier Ltd All rights reserved