10-deoxypyranicin | 1052734-56-1

• 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: 10-deoxypyranicin
• 英文别名: (2S)-4-[(2R,13R)-13-[(2R,5R,6R)-6-dodecyl-5-hydroxyoxan-2-yl]-2,13-dihydroxytridecyl]-2-methyl-2H-furan-5-one
• CAS: 1052734-56-1
• 化学式: C₃₅H₆₄O₆
• 分子量: 580.89
• InChiKey: MDLFVPARIQHWHX-YZDQYAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  41
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3R,6R)-6-{(1R,12R)-12-(tert-butyldimethylsilyloxy)-1-(methoxymethoxy)-13-[(5S)-5-methyl-3,4-dihydrofuran-2-on-3-yl]tridecyl}-2-dodecyl-3-(methoxymethoxy)tetrahydropyran 在 二甲基硫 、 三氟化硼乙醚 作用下， 反应 1.0h， 以74%的产率得到10-deoxypyranicin
  参考文献：
  名称：

  Synthesis of pyranicin and its deoxygenated analogues and their inhibitory action with bovine heart mitochondrial complex I

  摘要：

  Total synthesis of pyranicin and its deoxygenated analogues was achieved using Cl(2)Pd(CH(3)CN)(2) catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of these compounds for mitochondrial NADH-ubiquinone oxicloreductase (complex I) was poorer than those of ordinary mono-THF acetogenins such as annonacin. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.028

文献信息

• Synthesis of pyranicin and its deoxygenated analogues and their inhibitory action with bovine heart mitochondrial complex I
  作者：Shin-ichi Furuhata、Yasunao Hattori、Motonori Okajima、Hiroyuki Konno、Masato Abe、Hideto Miyoshi、Tetsuhisa Goto、Hidefumi Makabe

  DOI：10.1016/j.tet.2008.06.028

  日期：2008.8

  Total synthesis of pyranicin and its deoxygenated analogues was achieved using Cl(2)Pd(CH(3)CN)(2) catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of these compounds for mitochondrial NADH-ubiquinone oxicloreductase (complex I) was poorer than those of ordinary mono-THF acetogenins such as annonacin. (C) 2008 Elsevier Ltd. All rights reserved.