Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-7-methyloctanoate | 172329-53-2

• 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: Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-7-methyloctanoate
• 英文别名: methyl (4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-7-methyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]octanoate
• CAS: 172329-53-2
• 化学式: C₂₁H₄₃NO₅Si
• 分子量: 417.662
• InChiKey: IHAGGSQWWZFLNO-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-7-methyloctanoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (5S,1'S)-5-<1'--3'-methylbutyl>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'--1'-<(tert-butyldimethylsilyl)oxy>-4'-methylpentyl>-1,3-thiazole 在 sodium tetrahydroborate 、 4 A molecular sieve 、 copper(II) oxide 、 copper dichloride 、 nickel dichloride 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 43.92h， 生成 Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-7-methyloctanoate
  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.