(S)-3-((S)-2-(2,3-dihydroxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzamido)-3-((S)-2-(2,3-dihydroxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzamido)-3-hydroxypropanoyloxy)propanoyloxy)-2-(2,3-dihydroxybenzamido)propanoic acid | 568591-96-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-3-((S)-2-(2,3-dihydroxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzamido)-3-((S)-2-(2,3-dihydroxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzamido)-3-hydroxypropanoyloxy)propanoyloxy)-2-(2,3-dihydroxybenzamido)propanoic acid
• 英文别名: salmochelin S2；(2S)-2-[(2,3-dihydroxybenzoyl)amino]-3-[(2S)-2-[[2,3-dihydroxy-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]benzoyl]amino]-3-[(2S)-2-[[2,3-dihydroxy-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]benzoyl]amino]-3-hydroxypropanoyl]oxypropanoyl]oxypropanoic acid
• CAS: 568591-96-8
• 化学式: C₄₂H₄₉N₃O₂₆
• 分子量: 1011.86
• InChiKey: SRSLUJSVVOXLBP-VUCKQUTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  71
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  499
• 氢给体数：
  19
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  (S)-benzyl 3-((S)-3-((S)-3-(benzyloxy)-2-(2,3-bis(benzyloxy)-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzamido)propanoyloxy)-2-(2,3-bis(benzyloxy)-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzamido)propanoyloxy)-2-(2,3-bis(benzyloxy)benzamido)propanoate 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 18.05h， 生成 (S)-3-((S)-2-(2,3-dihydroxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzamido)-3-((S)-2-(2,3-dihydroxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzamido)-3-hydroxypropanoyloxy)propanoyloxy)-2-(2,3-dihydroxybenzamido)propanoic acid
  参考文献：
  名称：

  Facile synthesis of salmochelin S1, S2, MGE, DGE, and TGE

  摘要：

  Salmochelin S1, S2, MGE, DGE, and TGE were prepared through amide bond connection of an aryl C-glucosyl acyl chloride ((ArCOCl)-C-1) and serine ester amines, followed by hydrogenolysis of the per-benzylated precursors. Each synthesis employed a highly diastereoselective Ni-catalyzed Negishi approach to the aryl C-glycoside subunit. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.007