(2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal | 145655-02-3

• 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: (2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal
• 英文别名: tert-butyl N-benzyl-N-[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-4-oxo-1-phenylbutan-2-yl]carbamate
• CAS: 145655-02-3
• 化学式: C₂₈H₄₁NO₄Si
• 分子量: 483.723
• InChiKey: UJMLUFXKZMGAST-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal 在 sodium tetrahydroborate 、 四丁基氟化铵 、 水 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 65.0h， 生成 (5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Homologation of L-phenylalanine to ketomethylene and hydroxyethylene dipeptide isosteres via 2-thiazolyl amino ketone intermediate

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)60888-2
• 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 以83%的产率得到(2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal
  参考文献：
  名称：

  Homologation of L-phenylalanine to ketomethylene and hydroxyethylene dipeptide isosteres via 2-thiazolyl amino ketone intermediate

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)60888-2

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.
• 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.