5,6-dihydrovaltrate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5,6-dihydrovaltrate
• 英文别名: isodidrovaltrate；[(1S,4aS,6S,7R,7aS)-4-(acetyloxymethyl)-1-(3-methylbutanoyloxy)spiro[4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-6-yl] 3-methylbutanoate
• 化学式: C₂₂H₃₂O₈
• 分子量: 424.491
• InChiKey: KQEOKUJOWVGWDX-PNBTUHDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  异戊酸 、 (1S,4aS,6R,7R,7aS)-4-(acetoxymethyl)-6-hydroxy-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 以85%的产率得到5,6-dihydrovaltrate
  参考文献：
  名称：

  Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev

  摘要：

  Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (2) as the bioisostere of valtrate (1), the Rev-export inhibitor with anti-HIV activity. The synthesis of 2 was accomplished by ingenious use of asymmetric Diels-Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to 1, the analog 2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.038

文献信息

• Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev
  作者：Satoru Tamura、Nobuhiro Shimizu、Katsuaki Fujiwara、Masafumi Kaneko、Tominori Kimura、Nobutoshi Murakami

  DOI：10.1016/j.bmcl.2010.02.038

  日期：2010.4

  Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (2) as the bioisostere of valtrate (1), the Rev-export inhibitor with anti-HIV activity. The synthesis of 2 was accomplished by ingenious use of asymmetric Diels-Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to 1, the analog 2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy. (C) 2010 Elsevier Ltd. All rights reserved.