(2R,3R,4R,5R)-benzyl 2-(benzyloxymethyl)-5-(3,4-dimethoxyphenyl)-3,4-dihydroxypyrrolidine-1-carboxylate | 1214915-02-2

• 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)-benzyl 2-(benzyloxymethyl)-5-(3,4-dimethoxyphenyl)-3,4-dihydroxypyrrolidine-1-carboxylate
• 英文别名: benzyl (2R,3R,4R,5R)-2-(3,4-dimethoxyphenyl)-3,4-dihydroxy-5-(phenylmethoxymethyl)pyrrolidine-1-carboxylate
• CAS: 1214915-02-2
• 化学式: C₂₈H₃₁NO₇
• 分子量: 493.557
• InChiKey: JYHXKGLTCMSJOA-UUSJWDGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-benzyl 2-(benzyloxymethyl)-5-(3,4-dimethoxyphenyl)-3,4-dihydroxypyrrolidine-1-carboxylate 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到(2R,3R,4R,5R)-2-(benzyloxymethyl)-5-(3,4-dimethoxyphenyl)-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
• 作为产物：
  描述：

  benzyl (R)-2-(benzyloxy)-1-((4R,5R)-5-((3,4-dimethoxy-phenyl)(hydroxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到(2R,3R,4R,5R)-benzyl 2-(benzyloxymethyl)-5-(3,4-dimethoxyphenyl)-3,4-dihydroxypyrrolidine-1-carboxylate
  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

• 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