(3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one | 172329-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 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: tert-butyl N-benzyl-N-[(1S)-3-methyl-1-[(2S,4R)-4-(2-methylprop-2-enyl)-5-oxooxolan-2-yl]butyl]carbamate
• CAS: 172329-59-8
• 化学式: C₂₅H₃₇NO₄
• 分子量: 415.573
• InChiKey: XMISPJAZTPCISA-FSSWDIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one 在 palladium dihydroxide 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 18.17h， 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 、 mercury dichloride 、 nickel dichloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 、 乙腈 为溶剂， 反应 79.42h， 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

文献信息

• Thiazole-Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isostere Inhibitors of Renin and HIV-1 Aspartic Protease
  作者：Alessandro Dondoni、Daniela Perrone、M. Teresa Semola

  DOI：10.1021/jo00129a037

  日期：1995.12

  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.