benzyl (4S)-3-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-2-(2-hydroxyphenyl)-1,3-oxazolidine-4-carboxylate | 1220106-69-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: benzyl (4S)-3-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-2-(2-hydroxyphenyl)-1,3-oxazolidine-4-carboxylate
• CAS: 1220106-69-3
• 化学式: C₃₇H₃₄N₂O₇
• 分子量: 618.686
• InChiKey: IOAVOBORFIIIRT-SVYHFPLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (4S)-3-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-2-(2-hydroxyphenyl)-1,3-oxazolidine-4-carboxylate 在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 0.08h， 生成 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolyl-L-serine benzyl ester
  参考文献：
  名称：

  Salicylaldehyde Ester-Induced Chemoselective Peptide Ligations: Enabling Generation of Natural Peptidic Linkages at the Serine/Threonine Sites

  摘要：

  A serine/threonine-based chemoselective ligation method is described. It uses an O-salicylaldehyde ester at the C-terminus, reacting with N-terminal serine or threonine to realize peptide ligations. The utility of the O-salicylaldehyde ester enables the rapid coupling reaction and the production of an N,O-benzylidene acetal intermediate, which is readily converted into natural peptidic linkages (Xaa-Ser/Thr) at the ligation site.

  DOI：

  10.1021/ol1003109
• 作为产物：
  描述：

  1-((9H-fluoren-9-yl)methyl) 2-(2-formylphenyl) (S)-pyrrolidine-1,2-dicarboxylate 、 L-丝氨酸苄酯盐酸盐 在 吡啶 、 溶剂黄146 作用下， 反应 5.0h， 生成 benzyl (4S)-3-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]-2-(2-hydroxyphenyl)-1,3-oxazolidine-4-carboxylate
  参考文献：
  名称：

  Salicylaldehyde Ester-Induced Chemoselective Peptide Ligations: Enabling Generation of Natural Peptidic Linkages at the Serine/Threonine Sites

  摘要：

  A serine/threonine-based chemoselective ligation method is described. It uses an O-salicylaldehyde ester at the C-terminus, reacting with N-terminal serine or threonine to realize peptide ligations. The utility of the O-salicylaldehyde ester enables the rapid coupling reaction and the production of an N,O-benzylidene acetal intermediate, which is readily converted into natural peptidic linkages (Xaa-Ser/Thr) at the ligation site.

  DOI：

  10.1021/ol1003109

文献信息

• Salicylaldehyde Ester-Induced Chemoselective Peptide Ligations: Enabling Generation of Natural Peptidic Linkages at the Serine/Threonine Sites
  作者：Xuechen Li、Hiu Yung Lam、Yinfeng Zhang、Chun Kei Chan

  DOI：10.1021/ol1003109

  日期：2010.4.16

  A serine/threonine-based chemoselective ligation method is described. It uses an O-salicylaldehyde ester at the C-terminus, reacting with N-terminal serine or threonine to realize peptide ligations. The utility of the O-salicylaldehyde ester enables the rapid coupling reaction and the production of an N,O-benzylidene acetal intermediate, which is readily converted into natural peptidic linkages (Xaa-Ser/Thr) at the ligation site.