N-Boc-L-Pro-L-(OTBS)Ser methyl ester | 662722-96-5

• 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: N-Boc-L-Pro-L-(OTBS)Ser methyl ester
• 英文别名: Boc-Pro-Ser(TBDMS)-OMe；tert-butyl (2S)-2-[[(2S)-3-[tert-butyl(dimethyl)silyl]oxy-1-methoxy-1-oxopropan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 662722-96-5
• 化学式: C₂₀H₃₈N₂O₆Si
• 分子量: 430.617
• InChiKey: IYDATCNRPWGQTM-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Boc-L-Pro-L-(OTBS)Ser methyl ester 在 劳森试剂 、 manganese(IV) oxide 、 伯吉斯试剂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 Boc-L-Pro-Thz-OMe
  参考文献：
  名称：

  The first total synthesis of aeruginosamide

  摘要：

  要合成铜绿微囊藻的代谢产物铜绿素酰胺，需要克服聚合路线中遇到的困难，以及受最后一步条件制约的产物构象的有趣变化。

  DOI：

  10.1039/b515571a
• 作为产物：
  描述：

  BOC-L-脯氨酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 N-Boc-L-Pro-L-(OTBS)Ser methyl ester
  参考文献：
  名称：

  N ‐Terminal Selective C−H Azidation of Proline‐Containing Peptides: a Platform for Late‐Stage Diversification

  摘要：

  AbstractA methodology for the C−H azidation of N‐terminal proline‐containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at the carbamate‐protected N‐terminal residue in presence of the numerous other functional groups present on the molecules. Post‐functionalizations of the obtained aminal compounds were achieved: cycloaddition reactions or C−C bond formations via a sequence of imine formation/nucleophilic addition were performed, offering an easy access to diversified peptides.

  DOI：

  10.1002/chem.202200368

文献信息

• <i>N</i> ‐Terminal Selective C−H Azidation of Proline‐Containing Peptides: a Platform for Late‐Stage Diversification
  作者：Emmanuelle M. D. Allouche、Raphaël Simonet‐Davin、Jerome Waser

  DOI：10.1002/chem.202200368

  日期：2022.3.22

  AbstractA methodology for the C−H azidation of N‐terminal proline‐containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at the carbamate‐protected N‐terminal residue in presence of the numerous other functional groups present on the molecules. Post‐functionalizations of the obtained aminal compounds were achieved: cycloaddition reactions or C−C bond formations via a sequence of imine formation/nucleophilic addition were performed, offering an easy access to diversified peptides.
• The first total synthesis of aeruginosamide
  作者：Zhiyong Chen、Tao Ye

  DOI：10.1039/b515571a

  日期：——

  Synthesis of aeruginosamide, a metabolite of the cyanobacterium Microcystis aeruginosa, required overcoming difficulties encountered in a convergent route and an interesting change in conformation of the product governed by the conditions for the final step.

  要合成铜绿微囊藻的代谢产物铜绿素酰胺，需要克服聚合路线中遇到的困难，以及受最后一步条件制约的产物构象的有趣变化。