benzyl 3(R)-<(tert-butoxycarbonylamino)>-1-tetradecanoate

• 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: benzyl 3(R)-<(tert-butoxycarbonylamino)>-1-tetradecanoate
• 英文别名: benzyl (3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]tetradecanoate
• 化学式: C₂₆H₄₃NO₄
• 分子量: 433.632
• InChiKey: SYMYJWSWFIZVJE-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  31
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3(R)-<(tert-butoxycarbonylamino)>-1-tetradecanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到3(R)-<(tert-butoxycarbonylamino)>-1-tetradecanoic acid
  参考文献：
  名称：

  Synthesis of (R)-(+)-Boc-Iturinic Acid (n-C₁₄) from Aspartic Acid

  摘要：

  The first enantiospecific synthesis of the n-C14 isomer of iturinic acid, suitably protected for peptide synthesis, is presented. A new method for the synthesis of enantiomerically pure beta-amino acids from aspartic acid is used. The key step consists of an organocuprate addition to a tosylate derivative of aspartic acid, reduced at the alpha-carboxylic acid.

  DOI：

  10.1080/00397919508011380
• 作为产物：
  描述：

  1-氯癸烷 、 benzyl 3(S)-<(tert-butoxycarbonylamino)>-4-p-toluenesulfonyl-1-butyrate 在 copper(l) iodide 、 lithium 作用下， 生成 benzyl 3(R)-<(tert-butoxycarbonylamino)>-1-tetradecanoate
  参考文献：
  名称：

  Synthesis of (R)-(+)-Boc-Iturinic Acid (n-C₁₄) from Aspartic Acid

  摘要：

  The first enantiospecific synthesis of the n-C14 isomer of iturinic acid, suitably protected for peptide synthesis, is presented. A new method for the synthesis of enantiomerically pure beta-amino acids from aspartic acid is used. The key step consists of an organocuprate addition to a tosylate derivative of aspartic acid, reduced at the alpha-carboxylic acid.

  DOI：

  10.1080/00397919508011380

文献信息

• Synthesis of (<i>R</i>)-(+)-Boc-Iturinic Acid (n-C₁₄) from Aspartic Acid
  作者：John M. Bland

  DOI：10.1080/00397919508011380

  日期：1995.2

  The first enantiospecific synthesis of the n-C14 isomer of iturinic acid, suitably protected for peptide synthesis, is presented. A new method for the synthesis of enantiomerically pure beta-amino acids from aspartic acid is used. The key step consists of an organocuprate addition to a tosylate derivative of aspartic acid, reduced at the alpha-carboxylic acid.