Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate | 145655-06-7

• 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: Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate
• CAS: 145655-06-7
• 化学式: C₃₁H₄₇NO₅Si
• 分子量: 541.803
• InChiKey: QOHKKNGXMUNTSN-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.38
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate 在 sodium tetrahydroborate 、 溶剂黄146 、 三氟乙酸 、 nickel dichloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 29.92h， 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
• 作为产物：
  描述：

  (1'R,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-3-phenylpropyl>-1,3-thiazole 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 4 A molecular sieve 、 三乙胺 、 mercury dichloride 、 nickel dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 50.67h， 生成 Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate
  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

• Homologation of L-phenylalanine to ketomethylene and hydroxyethylene dipeptide isosteres via 2-thiazolyl amino ketone intermediate
  作者：Alessandro Dondoni、Daniela Perrone

  DOI：10.1016/s0040-4039(00)60888-2

  日期：1992.11

  A highly efficient route is presented for the synthesis of N-protected isosteric dipeptides Phepsi[COCH2]Gly and Phepsi[CH(OH)CH2]Phe from L-phenylalanine through 2-thiazolyl alpha-amino ketone and delta-amino-gamma-hydroxy-(E)-alpha,beta-enoate derivatives as key intermediates.