(R)-2-(((2R,3S)-3-((tert-butyldimethylsilyloxy)methyl)aziridin-2-yl)methylamino)-3-methyl-N-phenylbutanamide | 1000072-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-(((2R,3S)-3-((tert-butyldimethylsilyloxy)methyl)aziridin-2-yl)methylamino)-3-methyl-N-phenylbutanamide
• 英文别名: (R)-2-(((2R,5S)-3-((tert-butyldimethylsilyloxy)methyl)aziridin-2-yl)methylamino)-3-methyl-N-phenylbutanamide；(2R)-2-[[(2R,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]aziridin-2-yl]methylamino]-3-methyl-N-phenylbutanamide
• CAS: 1000072-81-0
• 化学式: C₂₁H₃₇N₃O₂Si
• 分子量: 391.629
• InChiKey: GLNUGKUVTSHWAQ-GUDVDZBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-valine anilide 、 (2S,4S,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]aziridin-2-yl]-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (R)-2-(((2R,3S)-3-((tert-butyldimethylsilyloxy)methyl)aziridin-2-yl)methylamino)-3-methyl-N-phenylbutanamide
  参考文献：
  名称：

  Epimerization- and Protecting-Group-Free Synthesis of Peptidomimetic Conjugates from Amphoteric Amino Aldehydes

  摘要：

  We have developed a novel protecting-group-free strategy for the synthesis of peptidomimetic conjugates. The high degrees of stereocontrol and chemoselectivity achieved in this chemistry hinge upon unusual preferences of the amphoteric amino aldehydes. The resulting conjugates contain reduced amide bonds at defined positions, offering a possibility for peptidomimetic ligation. These findings should allow access to templates for introducing both natural and unnatural amino acid residues in close proximity to the reduced amide bond isosteres.

  DOI：

  10.1021/ja076155p

文献信息

• Epimerization- and Protecting-Group-Free Synthesis of Peptidomimetic Conjugates from Amphoteric Amino Aldehydes
  作者：Xinghan Li、Andrei K. Yudin

  DOI：10.1021/ja076155p

  日期：2007.11.1

  We have developed a novel protecting-group-free strategy for the synthesis of peptidomimetic conjugates. The high degrees of stereocontrol and chemoselectivity achieved in this chemistry hinge upon unusual preferences of the amphoteric amino aldehydes. The resulting conjugates contain reduced amide bonds at defined positions, offering a possibility for peptidomimetic ligation. These findings should allow access to templates for introducing both natural and unnatural amino acid residues in close proximity to the reduced amide bond isosteres.