3-ethoxycarbonyl-2-methyl-5-[4'-deoxy-4'-[2-methyl-5-(D-arabino-tetritol-1'-yl)-3-furamide]-D-arabino-tetritol-1'-yl]furan | 551937-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-ethoxycarbonyl-2-methyl-5-[4'-deoxy-4'-[2-methyl-5-(D-arabino-tetritol-1'-yl)-3-furamide]-D-arabino-tetritol-1'-yl]furan
• 英文别名: ethyl 2-methyl-5-[(1S,2R,3R)-1,2,3-trihydroxy-4-[[2-methyl-5-[(1S,2R,3R)-1,2,3,4-tetrahydroxybutyl]furan-3-carbonyl]amino]butyl]furan-3-carboxylate
• CAS: 551937-40-7
• 化学式: C₂₂H₃₁NO₁₂
• 分子量: 501.488
• InChiKey: WJLDTLJMYBBDHI-YFYJLLRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  223
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-ethoxycarbonyl-2-methyl-5-[4'-deoxy-4'-[2-methyl-5-(D-arabino-tetritol-1'-yl)-3-furamide]-D-arabino-tetritol-1'-yl]furan 在 吡啶 作用下， 反应 12.0h， 生成 3-ethoxycarbonyl-2-methyl-5-[1',2',3'-tri-O-acetyl-4'-deoxy-4'-[2-methyl-5-(1',2',3',4'-tetra-O-acetyl-D-arabino-tetritol-1'-yl)-3-furamide]-D-arabino-tetritol-1'-yl]furan
  参考文献：
  名称：

  戊烯-类肽的溶液和固相合成。一种新型的拟肽

  摘要：

  通过使用羟烷基呋喃-氨基酸7作为新型支架合成亚戊二烯-类肽类化合物，已经证明可以容易地获得一类新型的拟肽。

  DOI：

  10.1016/s0040-4039(00)02266-8
• 作为产物：
  描述：

  5-(D-arabino-tetroxybutyl)-3-methyl-furoic acid 在 吡啶 、 2,2'-二硫二吡啶 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-ethoxycarbonyl-2-methyl-5-[4'-deoxy-4'-[2-methyl-5-(D-arabino-tetritol-1'-yl)-3-furamide]-D-arabino-tetritol-1'-yl]furan
  参考文献：
  名称：

  Hetaryleneaminopolyols and Hetarylenecarbopeptoids:  a New Type of Glyco- and Peptidomimetics. Syntheses and Studies on Solution Conformation and Dynamics

  摘要：

  Ready access to a new class of oligomers has been demonstrated by the synthesis of hetarylene-aminopolyols and hetarylenecarbopeptoids using 3-hydroxymethyl-5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methylfuran and 5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methyl-3-furoic acid as novel scaffolds. The conformational behavior of peptidomimetics 22, 23, 25, 26, and 36 have been analyzed by NMR spectroscopy and extensive molecular dynamics simulations. MD simulations using the GB/SA continuum solvent model for water and the MM3* force field provide a population distribution of conformers which satisfactorily agrees with the experimental NMR data for the torsional degrees of freedom of the molecule.

  DOI：

  10.1021/jo026631o

文献信息

• Solution and solid phase synthesis of hetarylene-carbopeptoids. A new type of peptidomimetics
  作者：A.J Moreno-Vargas、J.G Fernández-Bolaños、J Fuentes、I Robina

  DOI：10.1016/s0040-4039(00)02266-8

  日期：2001.2

  Ready access to a new class of peptidomimetics has been demonstrated by the synthesis of hetarylene-carbopeptoids using a hydroxyalkylfuran-aminoacid 7 as a novel scaffold.

  通过使用羟烷基呋喃-氨基酸7作为新型支架合成亚戊二烯-类肽类化合物，已经证明可以容易地获得一类新型的拟肽。
• Hetaryleneaminopolyols and Hetarylenecarbopeptoids:  a New Type of Glyco- and Peptidomimetics. Syntheses and Studies on Solution Conformation and Dynamics
  作者：Antonio J. Moreno-Vargas、Jesús Jiménez-Barbero、Inmaculada Robina

  DOI：10.1021/jo026631o

  日期：2003.5.1

  Ready access to a new class of oligomers has been demonstrated by the synthesis of hetarylene-aminopolyols and hetarylenecarbopeptoids using 3-hydroxymethyl-5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methylfuran and 5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methyl-3-furoic acid as novel scaffolds. The conformational behavior of peptidomimetics 22, 23, 25, 26, and 36 have been analyzed by NMR spectroscopy and extensive molecular dynamics simulations. MD simulations using the GB/SA continuum solvent model for water and the MM3* force field provide a population distribution of conformers which satisfactorily agrees with the experimental NMR data for the torsional degrees of freedom of the molecule.