methyl 6-[(2S,3S,4S,5R)-5-[[(2S,3S,4S,5R)-4-[(2S,3S,4R,5R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-[[(2S,3S,4R,5R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3-hydroxyoxolan-2-yl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]oxyhexanoate | 1373616-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-[(2S,3S,4S,5R)-5-[[(2S,3S,4S,5R)-4-[(2S,3S,4R,5R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-[[(2S,3S,4R,5R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3-hydroxyoxolan-2-yl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]oxyhexanoate
• CAS: 1373616-57-9
• 化学式: C₃₇H₆₂O₂₇
• 分子量: 938.883
• InChiKey: NCNKWHLBWXQKFK-WPQLISNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.5
• 重原子数：
  64
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  400
• 氢给体数：
  13
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  在 ammonium cerium (IV) nitrate 、 氨 作用下， 以 水 、 乙腈 、 甲醇 为溶剂， 反应 24.0h， 以82%的产率得到methyl 6-[(2S,3S,4S,5R)-5-[[(2S,3S,4S,5R)-4-[(2S,3S,4R,5R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-[[(2S,3S,4R,5R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3-hydroxyoxolan-2-yl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]oxyhexanoate
  参考文献：
  名称：

  Concise synthesis of an arabinofuranose hexasaccharide present in the cell wall of Mycobacterium tuberculosis

  摘要：

  Mycobacterium cell wall consists of three major polysaccharide portions and arabinofuranose (Araf) is present in two of the major portions, arabinogalactan (AG) and lipoarabinomannan (LAM). A peculiar Araf hexasaccharide possessing two beta-linked Araf units are present in both AG and LAM polysaccharides. Herein, we report an efficient and concise synthesis of this Araf hexasaccharide using single starting 3,5-TIPDS protected Araf thioglycoside precursor. Double beta-glycosylation was achieved using strained cyclic 2-p-methoxybenzyl-3,5-TIPDS Araf thioglycoside donor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.016