(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[2-[4-[6-[6-[2-[6-[2-[6-[2-[6-[2-[6-[2-[6-(3-hydroxy-3-methylbut-1-ynyl)-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]hex-5-ynyl]triazol-1-yl]ethoxy]oxane-3,4,5-triol | 1378991-59-3

• 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: (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[2-[4-[6-[6-[2-[6-[2-[6-[2-[6-[2-[6-[2-[6-(3-hydroxy-3-methylbut-1-ynyl)-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]hex-5-ynyl]triazol-1-yl]ethoxy]oxane-3,4,5-triol
• CAS: 1378991-59-3
• 化学式: C₁₀₉H₁₄₅N₉O₁₃
• 分子量: 1789.4
• InChiKey: VGOGYQWQVUHCPO-XFUMQCNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.4
• 重原子数：
  131
• 可旋转键数：
  70
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  283
• 氢给体数：
  5
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  2-Methyl-4-[6-[2-[6-[2-[6-[2-[6-[2-[6-[2-(6-octa-1,7-diynyl-4-octoxypyridin-2-yl)ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]but-3-yn-2-ol 、 2-azidoethyl α-D-mannopyranoside 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 44.5h， 以73%的产率得到(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[2-[4-[6-[6-[2-[6-[2-[6-[2-[6-[2-[6-[2-[6-(3-hydroxy-3-methylbut-1-ynyl)-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]ethynyl]-4-octoxypyridin-2-yl]hex-5-ynyl]triazol-1-yl]ethoxy]oxane-3,4,5-triol
  参考文献：
  名称：

  Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction

  摘要：

  Based on 'click chemistry', the new convergent synthesis to a variety of saccharide-linked 2,6-pyridylene ethynylene 'ethynylpyridine' foldamers was developed. Ethynylpyridine 6-, 9-, and 12-meric blocks were linked with 1,7-octadiyne linker block by Sonogashira reaction, and joined with azido group-introduced glucoside, galactoside, and mannoside templates by Huisgen reaction. The resulting saccharide-linked ethynylpyridine foldamers exhibited typical circular dichroism to indicate the formation of a helical structure by intramolecular hydrogen bonds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.069

文献信息

• Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction
  作者：Hajime Abe、Hiroki Makida、Masahiko Inouye

  DOI：10.1016/j.tet.2012.02.069

  日期：2012.6

  Based on 'click chemistry', the new convergent synthesis to a variety of saccharide-linked 2,6-pyridylene ethynylene 'ethynylpyridine' foldamers was developed. Ethynylpyridine 6-, 9-, and 12-meric blocks were linked with 1,7-octadiyne linker block by Sonogashira reaction, and joined with azido group-introduced glucoside, galactoside, and mannoside templates by Huisgen reaction. The resulting saccharide-linked ethynylpyridine foldamers exhibited typical circular dichroism to indicate the formation of a helical structure by intramolecular hydrogen bonds. (C) 2012 Elsevier Ltd. All rights reserved.