[(2R,3S,4S,5R,6R)-3,5-diacetyloxy-6-[(2R,3R,4R,5S,6R)-2-(2-azidoethoxy)-3-(1,3-dioxoisoindol-2-yl)-5-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-4-[(4-methoxyphenyl)methoxy]oxan-2-yl]methyl acetate | 864270-49-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4S,5R,6R)-3,5-diacetyloxy-6-[(2R,3R,4R,5S,6R)-2-(2-azidoethoxy)-3-(1,3-dioxoisoindol-2-yl)-5-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-4-[(4-methoxyphenyl)methoxy]oxan-2-yl]methyl acetate
• CAS: 864270-49-5
• 化学式: C₇₀H₇₆N₄O₂₀
• 分子量: 1293.39
• InChiKey: IZFAPEWKVQBZEV-CEQJRGSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  94
• 可旋转键数：
  33
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  241
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6R)-3,5-diacetyloxy-6-[(2R,3R,4R,5S,6R)-2-(2-azidoethoxy)-3-(1,3-dioxoisoindol-2-yl)-5-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-4-[(4-methoxyphenyl)methoxy]oxan-2-yl]methyl acetate 在 四丁基碘化铵 、 sodium hydride 、 乙二胺 、 正丁醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N-[(2R,3R,4R,5S,6R)-2-(2-azidoethoxy)-4-[(2R,3R,4S,5S,6R)-4-[(4-methoxyphenyl)methoxy]-3,5-bis(prop-2-enoxy)-6-(prop-2-enoxymethyl)oxan-2-yl]oxy-5-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-3-yl]-N-prop-2-enylacetamide
  参考文献：
  名称：

  Pentaerythritol as the Core of Multivalent Glycolipids:  Synthesis of a Glycolipid with Three SO₃Le^a Ligands

  摘要：

  [GRAPHICS]A glycolipid containing three SO(3)Le(a) ligands was synthesized with pentaerythritol as the core. The glycolipid was used to prepare glycoliposomes that showed stability similar to that of DSPC liposomes without glycolipid. The easily prepared derivatives of pentaerythritol proved to be useful scaffolds for multivalent displaying of carbohydrates in the form of glycolipids and clustered glycoliposomes.

  DOI：

  10.1021/ol0514202
• 作为产物：
  描述：

  2-[(2R,3R,4R,5S,6R)-2-(2-Azido-ethoxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 在 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 camphor-10-sulfonic acid 、 四丁基溴化铵 、 sodium cyanoborohydride 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.33h， 生成 [(2R,3S,4S,5R,6R)-3,5-diacetyloxy-6-[(2R,3R,4R,5S,6R)-2-(2-azidoethoxy)-3-(1,3-dioxoisoindol-2-yl)-5-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-4-[(4-methoxyphenyl)methoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Pentaerythritol as the Core of Multivalent Glycolipids:  Synthesis of a Glycolipid with Three SO₃Le^a Ligands

  摘要：

  [GRAPHICS]A glycolipid containing three SO(3)Le(a) ligands was synthesized with pentaerythritol as the core. The glycolipid was used to prepare glycoliposomes that showed stability similar to that of DSPC liposomes without glycolipid. The easily prepared derivatives of pentaerythritol proved to be useful scaffolds for multivalent displaying of carbohydrates in the form of glycolipids and clustered glycoliposomes.

  DOI：

  10.1021/ol0514202