1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-(naphthalen-1-ylmethylamino)pyrrolidine-1,2,4-tricarboxylate | 1205681-60-2

• 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: 1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-(naphthalen-1-ylmethylamino)pyrrolidine-1,2,4-tricarboxylate
• CAS: 1205681-60-2
• 化学式: C₃₄H₃₄N₆O₆
• 分子量: 622.681
• InChiKey: SZAAYOBKWIPKIG-GVYVVWIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-(naphthalen-1-ylmethylamino)pyrrolidine-1,2,4-tricarboxylate 、 (2'S,3S,7S,8aS)-2-benzyl-7-(9H-fluoren-9-ylmethoxycarbonylamino)-7-methoxycarbonyl-1,4-dioxospiro[8,8a-dihydro-6H-pyrrolo[1,2-a]pyrazine-3,4'-pyrrolidine]-2'-carboxylic acid 在 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 、 氢溴酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 1.5h， 以77%的产率得到
  参考文献：
  名称：

  Synthesis of Hexa- and Pentasubstituted Diketopiperazines from Sterically Hindered Amino Acids

  摘要：

  Steric hindrance assists in the formation of hindered diketopiperazines using acyl-transfer coupling. In acyl-transfer coupling, the carboxylate of an unprotected N-alkylamino acid attacks an active ester to form a transient anhydride that undergoes an O,N acyl transfer to form a tertiary amide. If the active ester is part of an N-alkylamino acid it will form a diketopiperazine. It is demonstrated here that acyl-transfer coupling can assemble highly functionalized bis-peptides bearing a functional group on every monomer.

  DOI：

  10.1021/ol100048g
• 作为产物：
  描述：

  N-羟基-7-氮杂苯并三氮唑 、 (3S,5S)-1-[(benzyloxy)carbonyl]-5-[(tert-butoxy)carbonyl]-3-[(naphthanlen-1-ylmethyl)amino]pyrrolidine-3-carboxylic acid 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1-O-benzyl 2-O-tert-butyl 4-O-(triazolo[4,5-b]pyridin-3-yl) (2S,4S)-4-(naphthalen-1-ylmethylamino)pyrrolidine-1,2,4-tricarboxylate
  参考文献：
  名称：

  Synthesis of Hexa- and Pentasubstituted Diketopiperazines from Sterically Hindered Amino Acids

  摘要：

  Steric hindrance assists in the formation of hindered diketopiperazines using acyl-transfer coupling. In acyl-transfer coupling, the carboxylate of an unprotected N-alkylamino acid attacks an active ester to form a transient anhydride that undergoes an O,N acyl transfer to form a tertiary amide. If the active ester is part of an N-alkylamino acid it will form a diketopiperazine. It is demonstrated here that acyl-transfer coupling can assemble highly functionalized bis-peptides bearing a functional group on every monomer.

  DOI：

  10.1021/ol100048g

文献信息

• Synthesis of Hexa- and Pentasubstituted Diketopiperazines from Sterically Hindered Amino Acids
  作者：Zachary Z. Brown、Christian E. Schafmeister

  DOI：10.1021/ol100048g

  日期：2010.4.2

  Steric hindrance assists in the formation of hindered diketopiperazines using acyl-transfer coupling. In acyl-transfer coupling, the carboxylate of an unprotected N-alkylamino acid attacks an active ester to form a transient anhydride that undergoes an O,N acyl transfer to form a tertiary amide. If the active ester is part of an N-alkylamino acid it will form a diketopiperazine. It is demonstrated here that acyl-transfer coupling can assemble highly functionalized bis-peptides bearing a functional group on every monomer.