N-[(2S,4aR,6R,7R,8R,8aR)-2-[(1R,2R,3R,4R)-1-acetamido-2,3,5-trihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentyl]-8-hydroxy-6-(4-methoxyphenoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide | 1132966-82-5

• 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: N-[(2S,4aR,6R,7R,8R,8aR)-2-[(1R,2R,3R,4R)-1-acetamido-2,3,5-trihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentyl]-8-hydroxy-6-(4-methoxyphenoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 1132966-82-5
• 化学式: C₂₉H₄₄N₂O₁₇
• 分子量: 692.672
• InChiKey: PJUNCSOFIOVQRM-HHEJAYOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  285
• 氢给体数：
  10
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  [(2S,4aR,6R,7R,8R,8aR)-7-azido-2-[(1R,2R,3R,4R)-1-azido-2,3,5-tris(phenylmethoxy)-4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentyl]-6-(4-methoxyphenoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate 、 乙酸酐 在 三乙基硅烷 、 10% Pd/C 、 吡啶 、 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 24.0h， 以82%的产率得到N-[(2S,4aR,6R,7R,8R,8aR)-2-[(1R,2R,3R,4R)-1-acetamido-2,3,5-trihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentyl]-8-hydroxy-6-(4-methoxyphenoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
  参考文献：
  名称：

  Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus

  摘要：

  The first stereoselective synthesis of a unique trisaccharide containing an open-chain glycosyl cyclic acetal moiety found in the cell wall of Proteus has been successfully achieved. Most of the intermediate steps are high yielding and highly reproducible. The acetal linkage of the open-chain D-galactosamine moiety with an (S)-configuration was formed exclusively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.006