(5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxohexanoic acid | 145242-39-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxohexanoic acid
• CAS: 145242-39-3
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: JGDREQXMBJOJFH-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 、 (5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxohexanoic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到N-((1S)-1-carbomethoxy-2-phenylethyl) (5S)-5-(t-butyloxycarbonyl)amino-4-oxohexanoamide
  参考文献：
  名称：

  Chain extension of amino acid skeletons: preparation of ketomethylene isosteres

  摘要：

  Ketomethylene isosteric replacements for peptide bonds were generated through a zinc carbenoid-mediated chain extension reaction in which a variety of amino acid-derived beta-keto esters are converted to gamma-keto esters in a single step. The reaction tolerates a variety of protecting groups and amino acid side chains with no epimerization of the amino acid stereocenter. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00052-8
• 作为产物：
  描述：

  phenylmethyl (4S)-4-(t-butyloxycarbonyl)amino-3-oxopentanoate 在 palladium on activated charcoal 氢气 、 diethylzinc 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxohexanoic acid
  参考文献：
  名称：

  Chain extension of amino acid skeletons: preparation of ketomethylene isosteres

  摘要：

  Ketomethylene isosteric replacements for peptide bonds were generated through a zinc carbenoid-mediated chain extension reaction in which a variety of amino acid-derived beta-keto esters are converted to gamma-keto esters in a single step. The reaction tolerates a variety of protecting groups and amino acid side chains with no epimerization of the amino acid stereocenter. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00052-8

文献信息

• Chain extension of amino acid skeletons: preparation of ketomethylene isosteres
  作者：Cory R Theberge、Charles K Zercher

  DOI：10.1016/s0040-4020(03)00052-8

  日期：2003.2

  Ketomethylene isosteric replacements for peptide bonds were generated through a zinc carbenoid-mediated chain extension reaction in which a variety of amino acid-derived beta-keto esters are converted to gamma-keto esters in a single step. The reaction tolerates a variety of protecting groups and amino acid side chains with no epimerization of the amino acid stereocenter. (C) 2003 Elsevier Science Ltd. All rights reserved.