(S)-Fmoc-β-nitroalaninyl-(R)-α-methylbenzylamide | 1235352-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-Fmoc-β-nitroalaninyl-(R)-α-methylbenzylamide
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2S)-3-nitro-1-oxo-1-[[(1R)-1-phenylethyl]amino]propan-2-yl]carbamate
• CAS: 1235352-53-0
• 化学式: C₂₆H₂₅N₃O₅
• 分子量: 459.502
• InChiKey: SNDJFFNMJIAWFD-OSPHWJPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-Fmoc-β-nitroalanine 、 R(+)-alpha-甲基苄胺 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以81%的产率得到(S)-Fmoc-β-nitroalaninyl-(R)-α-methylbenzylamide
  参考文献：
  名称：

  Efficient stereocontrolled synthesis of (S)-Fmoc-β-nitroalanine via oxidation of oxime

  摘要：

  Stereocontrolled synthesis of (S)-Fmoc-beta-nitroalanine (20) was accomplished from (R)-Fmoc-Ser((t)Bu)-OH (14) in a total of six steps via an oxime. The oxime (17) was obtained from (R)-Fmoc-Ser((t)Bu)-H (16). which in turn was obtained by reduction of Weinreb amide (15). Oxidation of oxime was realized with peroxytrifluoroacetic acid at a neutral pH at 0 degrees C. After removal of the (t)Bu protecting group with 90% TFA/H(2)O, the hydroxyl group was oxidized with Jones reagent to afford (S)-Fmoc-beta-nitroalanine (20) in overall good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.083

文献信息

• Efficient stereocontrolled synthesis of (S)-Fmoc-β-nitroalanine via oxidation of oxime
  作者：Satendra S. Chauhan、Howard J. Wilk

  DOI：10.1016/j.tetlet.2010.04.083

  日期：2010.6

  Stereocontrolled synthesis of (S)-Fmoc-beta-nitroalanine (20) was accomplished from (R)-Fmoc-Ser((t)Bu)-OH (14) in a total of six steps via an oxime. The oxime (17) was obtained from (R)-Fmoc-Ser((t)Bu)-H (16). which in turn was obtained by reduction of Weinreb amide (15). Oxidation of oxime was realized with peroxytrifluoroacetic acid at a neutral pH at 0 degrees C. After removal of the (t)Bu protecting group with 90% TFA/H(2)O, the hydroxyl group was oxidized with Jones reagent to afford (S)-Fmoc-beta-nitroalanine (20) in overall good yield. (C) 2010 Elsevier Ltd. All rights reserved.