1-N,2-N-bis[[1-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]triazol-4-yl]methyl]benzene-1,2-dicarboxamide | 1021875-48-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-N,2-N-bis[[1-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]triazol-4-yl]methyl]benzene-1,2-dicarboxamide
• CAS: 1021875-48-8
• 化学式: C₃₀H₄₂N₈O₁₄
• 分子量: 738.709
• InChiKey: DUSONDDYNZFKPW-KCLJBWGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  318
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[4-[[[2-[[1-[2-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyethyl]triazol-4-yl]methylcarbamoyl]benzoyl]amino]methyl]triazol-1-yl]ethoxy]oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以96%的产率得到1-N,2-N-bis[[1-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]triazol-4-yl]methyl]benzene-1,2-dicarboxamide
  参考文献：
  名称：

  Synthesis of novel multidentate carbohydrate-triazole ligands

  摘要：

  Cu(I)-catalyzed 1,3-dipolar cycloaddition (click reaction) of 1 mol equiv of N,N'-di-prop-2-ynyl-phthalamide (1a), N,N'-di-prop-2-ynyl-isophthalamide (1b), and pyridine-2,6-dicarboxylic acid bis-prop-2-ynylamide (1c), respectively with 2 mol equiv of 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide (2a), 2-azidoethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (2b), and 2-azidoethyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (2c), respectively, afforded the corresponding bis-cycloadducts 3-5, containing two 1,2,3-triazole moieties each, in 38-76% yield. Reaction of 1 mol equiv of 2c with 1 mol equiv of le under otherwise identical conditions gave the mono-cycloadduct 6, containing one 1,2,3-triazole and one 2-propynylamide moiety, in 77% yield. Reaction of 6 with 2a afforded 7, containing two different sugar moieties, in 67% yield. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.081

文献信息

• Synthesis of novel multidentate carbohydrate-triazole ligands
  作者：Thomas Ziegler、Catrin Hermann

  DOI：10.1016/j.tetlet.2008.01.081

  日期：2008.3

  Cu(I)-catalyzed 1,3-dipolar cycloaddition (click reaction) of 1 mol equiv of N,N'-di-prop-2-ynyl-phthalamide (1a), N,N'-di-prop-2-ynyl-isophthalamide (1b), and pyridine-2,6-dicarboxylic acid bis-prop-2-ynylamide (1c), respectively with 2 mol equiv of 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide (2a), 2-azidoethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (2b), and 2-azidoethyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (2c), respectively, afforded the corresponding bis-cycloadducts 3-5, containing two 1,2,3-triazole moieties each, in 38-76% yield. Reaction of 1 mol equiv of 2c with 1 mol equiv of le under otherwise identical conditions gave the mono-cycloadduct 6, containing one 1,2,3-triazole and one 2-propynylamide moiety, in 77% yield. Reaction of 6 with 2a afforded 7, containing two different sugar moieties, in 67% yield. (c) 2008 Elsevier Ltd. All rights reserved.