tert-butyl 2-hydroxy-4-[[(2S)-1-methoxy-1-oxo-6-[[(E)-3-phenylprop-2-enoyl]-(2-trimethylsilylethoxy)amino]hexan-2-yl]amino]-2-[2-[[(2S)-1-methoxy-1-oxo-6-[[(E)-3-phenylprop-2-enoyl]-(2-trimethylsilylethoxy)amino]hexan-2-yl]amino]-2-oxoethyl]-4-oxobutanoate | 183890-46-2

• 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: tert-butyl 2-hydroxy-4-[[(2S)-1-methoxy-1-oxo-6-[[(E)-3-phenylprop-2-enoyl]-(2-trimethylsilylethoxy)amino]hexan-2-yl]amino]-2-[2-[[(2S)-1-methoxy-1-oxo-6-[[(E)-3-phenylprop-2-enoyl]-(2-trimethylsilylethoxy)amino]hexan-2-yl]amino]-2-oxoethyl]-4-oxobutanoate
• CAS: 183890-46-2
• 化学式: C₅₂H₈₀N₄O₁₃Si₂
• 分子量: 1025.4
• InChiKey: KUGKOQQWPGXLDE-KXWDIBNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  71
• 可旋转键数：
  35
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  216
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-hydroxy-4-[[(2S)-1-methoxy-1-oxo-6-[[(E)-3-phenylprop-2-enoyl]-(2-trimethylsilylethoxy)amino]hexan-2-yl]amino]-2-[2-[[(2S)-1-methoxy-1-oxo-6-[[(E)-3-phenylprop-2-enoyl]-(2-trimethylsilylethoxy)amino]hexan-2-yl]amino]-2-oxoethyl]-4-oxobutanoate 在 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.5h， 生成 nannochelin A
  参考文献：
  名称：

  A Total Synthesis of Nannochelin A. A Short Route to Optically Active N^ω-Hydroxy-α-amino Acid Derivatives

  摘要：

  The total synthesis of nannochelin A, a lysine-basd cinnamoyl hydroxamate produced by Nannocystis exedens, is described. The key transformation involves construction of the N-epsilon-cinnamoyl-N-epsilon-hydroxy-L-lysine methyl ester fragment by partial reduction of the lactam carbonyl of 6 derived from L-lysine, oximation of this aldehyde equivalent compound 8 with O-[2-(trimethylsilyl)ethyl]hydroxylamine, and reduction of the oxime 10, followed by N-acylation prior to coupling with the external carbonyls of citric acid. This methodology will be applicable to synthesis of other hydroxamate-containing siderophores bearing hydrogenolyzable groups in the molecule.

  DOI：

  10.1021/jo961458f
• 作为产物：
  描述：

  (-)-(S)-6-oxo-2-piperidinecarboxylic acid methyl ester 在 盐酸 、 4-二甲氨基吡啶 、 吡啶硼烷 、 三乙基硼氢化锂 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 34.58h， 生成 tert-butyl 2-hydroxy-4-[[(2S)-1-methoxy-1-oxo-6-[[(E)-3-phenylprop-2-enoyl]-(2-trimethylsilylethoxy)amino]hexan-2-yl]amino]-2-[2-[[(2S)-1-methoxy-1-oxo-6-[[(E)-3-phenylprop-2-enoyl]-(2-trimethylsilylethoxy)amino]hexan-2-yl]amino]-2-oxoethyl]-4-oxobutanoate
  参考文献：
  名称：

  A Total Synthesis of Nannochelin A. A Short Route to Optically Active N^ω-Hydroxy-α-amino Acid Derivatives

  摘要：

  The total synthesis of nannochelin A, a lysine-basd cinnamoyl hydroxamate produced by Nannocystis exedens, is described. The key transformation involves construction of the N-epsilon-cinnamoyl-N-epsilon-hydroxy-L-lysine methyl ester fragment by partial reduction of the lactam carbonyl of 6 derived from L-lysine, oximation of this aldehyde equivalent compound 8 with O-[2-(trimethylsilyl)ethyl]hydroxylamine, and reduction of the oxime 10, followed by N-acylation prior to coupling with the external carbonyls of citric acid. This methodology will be applicable to synthesis of other hydroxamate-containing siderophores bearing hydrogenolyzable groups in the molecule.

  DOI：

  10.1021/jo961458f

文献信息

• A Total Synthesis of Nannochelin A. A Short Route to Optically Active <i>N</i>^ω-Hydroxy-α-amino Acid Derivatives
  作者：Takeshi Sakamoto、Hao Li、Yasuo Kikugawa

  DOI：10.1021/jo961458f

  日期：1996.1.1

  The total synthesis of nannochelin A, a lysine-basd cinnamoyl hydroxamate produced by Nannocystis exedens, is described. The key transformation involves construction of the N-epsilon-cinnamoyl-N-epsilon-hydroxy-L-lysine methyl ester fragment by partial reduction of the lactam carbonyl of 6 derived from L-lysine, oximation of this aldehyde equivalent compound 8 with O-[2-(trimethylsilyl)ethyl]hydroxylamine, and reduction of the oxime 10, followed by N-acylation prior to coupling with the external carbonyls of citric acid. This methodology will be applicable to synthesis of other hydroxamate-containing siderophores bearing hydrogenolyzable groups in the molecule.