(3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one | 172329-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one
• 英文别名: (3R,5S)-5-[(1S)-1-(benzylamino)-3-methylbutyl]-3-(2-methylprop-2-enyl)oxolan-2-one
• CAS: 172329-61-2
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: BEHJAIVASKGYSX-QYZOEREBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 (3R,5S,1'S)-5-<1'-<(N-tert-Butoxycarbonyl)amino>-3'-methylbutyl>-3-(2-methylpropyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Thiazole-Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isostere Inhibitors of Renin and HIV-1 Aspartic Protease

  摘要：

  A new synthesis of hydroxyethylene dipeptide isosteres for Leu-Leu and Phe-Phe in their gamma-lactone form 1a and 1b employing beta-amino-alpha-hydroxy aldehydes with singly and doubly protected nitrogen has been developed. These key intermediates, which are available through the thiazole-aldehyde synthesis from L-leucine and L-phenylalanine, were converted to alkanoates by Wittig olefination and reduction of the ethylenic double bond. Lactonization and stereoselective alkylation at C-2 of the resulting lactones completed the building up of the structural framework. Overall yields were in the range 16-19% for 1a and 22-23% for 1b.

  DOI：

  10.1021/jo00129a037
• 作为产物：
  描述：

  (1'R,2'S)-2-<2'-<(N-tert-Butoxycarbonyl)benzylamino>-1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole 在 sodium tetrahydroborate 、 4 A molecular sieve 、 溶剂黄146 、 三氟乙酸 、 mercury dichloride 、 nickel dichloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 79.59h， 生成 (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Thiazole-Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isostere Inhibitors of Renin and HIV-1 Aspartic Protease

  摘要：

  A new synthesis of hydroxyethylene dipeptide isosteres for Leu-Leu and Phe-Phe in their gamma-lactone form 1a and 1b employing beta-amino-alpha-hydroxy aldehydes with singly and doubly protected nitrogen has been developed. These key intermediates, which are available through the thiazole-aldehyde synthesis from L-leucine and L-phenylalanine, were converted to alkanoates by Wittig olefination and reduction of the ethylenic double bond. Lactonization and stereoselective alkylation at C-2 of the resulting lactones completed the building up of the structural framework. Overall yields were in the range 16-19% for 1a and 22-23% for 1b.

  DOI：

  10.1021/jo00129a037