arthrobacilin A | 142547-11-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: arthrobacilin A
• 英文别名: (1R,3R,8R,9R,10S,11R,12R,14R,19R,20R,21S,22R,23R,25R,30R,31R,32S,33R)-9,10,11,20,21,22,31,32,33-nonahydroxy-3,14,25-tri(nonyl)-2,6,13,17,24,28,34,35,36-nonaoxatetracyclo[28.3.1.18,12.119,23]hexatriacontane-5,16,27-trione
• CAS: 142547-11-3
• 化学式: C₅₄H₉₆O₂₁
• 分子量: 1081.34
• InChiKey: ZSOILIACAWNDPB-LAHGXSIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  75
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  316
• 氢给体数：
  9
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  (1R,3R,8R,9S,10S,11R,12R,14R,19R,20S,21S,22R,23R,25R,30R,31S,32S,33R)-3,14,25-tri(nonyl)-9,10,11,20,21,22,31,32,33-nonakis(phenylmethoxy)-2,6,13,17,24,28,34,35,36-nonaoxatetracyclo[28.3.1.18,12.119,23]hexatriacontane-5,16,27-trione 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 以96%的产率得到arthrobacilin A
  参考文献：
  名称：

  Total synthesis of arthrobacilin A

  摘要：

  Novel cyclic glycolipids, arthrobacilin A and its analogues, have been synthesized by means of unique DCC/DMAP.HCl promoted oligomerization/cyclization, zinc salt catalyzed beta-selective glycosylation, and Noyori's BINAP/Ru catalyzed asymmetric reduction.

  DOI：

  10.1016/s0040-4039(00)76898-5

文献信息

• Total synthesis of arthrobacilin A
  作者：Dulce M. Garcia、Hidetoshi Yamada、Susumi Hatakeyama、Mugio Nishizawa

  DOI：10.1016/s0040-4039(00)76898-5

  日期：1994.5

  Novel cyclic glycolipids, arthrobacilin A and its analogues, have been synthesized by means of unique DCC/DMAP.HCl promoted oligomerization/cyclization, zinc salt catalyzed beta-selective glycosylation, and Noyori's BINAP/Ru catalyzed asymmetric reduction.