3-oxo-5-phenyl-4S-(tritylamino)pentanoic acid allyl ester | 210580-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-oxo-5-phenyl-4S-(tritylamino)pentanoic acid allyl ester
• 英文别名: prop-2-enyl (4S)-3-oxo-5-phenyl-4-(tritylamino)pentanoate
• CAS: 210580-12-4
• 化学式: C₃₃H₃₁NO₃
• 分子量: 489.614
• InChiKey: ROUUHCZURQPJTL-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-oxo-5-phenyl-4S-(tritylamino)pentanoic acid allyl ester 在 吗啉 、 四(三苯基膦)钯 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-phenyl-2S-(tritylamino)undecan-3-one
  参考文献：
  名称：

  Highly Stereoselective Syntheses of syn- and anti-1,2-Amino Alcohols

  摘要：

  The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-BU)(3) in ethanol at -78 degreesC. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)(3) in THF at -5 degreesC.

  DOI：

  10.1021/jo010270f
• 作为产物：
  描述：

  N-trityl-L-phenylalanine 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-oxo-5-phenyl-4S-(tritylamino)pentanoic acid allyl ester
  参考文献：
  名称：

  Highly Stereoselective Syntheses of syn- and anti-1,2-Amino Alcohols

  摘要：

  The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-BU)(3) in ethanol at -78 degreesC. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)(3) in THF at -5 degreesC.

  DOI：

  10.1021/jo010270f

文献信息

• A Stereocontrolled Synthesis of Monofluoro Ketomethylene Dipeptide Isosteres
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1021/jo981334y

  日期：1999.1.1

  A simple, stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. N-Tritylated ketomethylene dipeptide isosteres, prepared from N-tritylated amino acids, are converted to their Z-TMS enol ethers and fluorinated with Selectfluor. There is cooperative stereocontrol between the N-tritylamine group and the alkyl group at C-2. The method is short (six steps), diastereoselective

  已经开发了简单的立体控制的单氟酮亚甲基二肽等排体的合成。由N-三苯甲基化的氨基酸制备的N-三苯甲基化的酮亚甲基二肽等位基因被转化为其Z-TMS烯醇醚并用Selectfluor进行氟化。N-三苯甲基胺基和C-2处的烷基之间存在协同立体控制。该方法很短（六个步骤），非对映选择性（85-> 95％）和对映选择性（> 95％）。
• A stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1016/s0040-4039(98)00783-7

  日期：1998.6

  A simple, stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. The method is short (6 steps) and diastereoselective (85–95% de) and enantioselective (>95% ee).

  已经开发出简单的立体控制的单氟酮亚甲基二肽等排体的合成方法。该方法很短（6个步骤），非对映选择性（85-95％de）和对映选择性（> 95％ee）。