(2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester | 862177-23-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester
• 英文别名: (3S,6S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonyl]-1-phenylmethoxycarbonylpiperidine-3-carboxylic acid
• CAS: 862177-23-9
• 化学式: C₃₄H₃₆N₂O₈
• 分子量: 600.668
• InChiKey: VSCRETWXMWKTQZ-GVYVVWIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 5-methyl ester
  参考文献：
  名称：

  Synthesis of a Pipecolic Acid-Based Bis-amino Acid and Its Assembly into a Spiro Ladder Oligomer

  摘要：

  The synthesis of a new pipecolic acid-based bis-amino acid building block 1 (and 2) is presented. Assembly of this monomer into a spiro ladder oligomer 3 utilizing solid-phase synthesis followed by in situ activation by dicyclohexylcarbodiimide and N-hydroxysuccinimide has been demonstrated. The structure of oligomer 3, determined in aqueous solution using two-dimensional NMR, reveals that the oligomer forms a left-handed helix and that each monomer unit adopts a chair conformation.

  DOI：

  10.1021/ol0507672
• 作为产物：
  描述：

  (2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 在 4-二甲氨基吡啶 、 potassium cyanide 、 氢氧化钾 、 三甲基氯硅烷 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 (2S,5S)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-piperidine-1,2,5-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester
  参考文献：
  名称：

  Synthesis of a Pipecolic Acid-Based Bis-amino Acid and Its Assembly into a Spiro Ladder Oligomer

  摘要：

  The synthesis of a new pipecolic acid-based bis-amino acid building block 1 (and 2) is presented. Assembly of this monomer into a spiro ladder oligomer 3 utilizing solid-phase synthesis followed by in situ activation by dicyclohexylcarbodiimide and N-hydroxysuccinimide has been demonstrated. The structure of oligomer 3, determined in aqueous solution using two-dimensional NMR, reveals that the oligomer forms a left-handed helix and that each monomer unit adopts a chair conformation.

  DOI：

  10.1021/ol0507672

文献信息

• Synthesis of Structurally Diverse Bis-peptide Oligomers
  作者：Sharad Gupta、Megan Macala、Christian E. Schafmeister

  DOI：10.1021/jo0609125

  日期：2006.11.1

  We have developed second-generation monomers 1 and 2 and improved conditions for rapidly and simultaneously closing multiple diketopiperazines on solid support. These new conditions involve either the microwave heating of a suspension of solid-supported amino-tetrafluoropropyl esters in acetic acid/triethylamine catalyst solution or continuous flow of catalyst solution through the resin, heated in

  我们已经开发出第二代单体1和2，并改善了条件，可以快速同时封闭固体载体上的多种二酮哌嗪。这些新条件包括在加热流动池设备中微波加热固体负载的氨基四氟丙基酯在乙酸/三乙胺催化剂溶液中的悬浮液，或使催化剂溶液连续流过树脂。我们证明，新的单体1和2可以与新的条件轻松地合成以前无法获得的杂和同螺形梯形低聚物3和4等。