N-tert-butoxycarbonyl-5-triphenylmethylthiomethyl-L-proline tert-butyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-tert-butoxycarbonyl-5-triphenylmethylthiomethyl-L-proline tert-butyl ester
• 英文别名: ditert-butyl (2S)-5-(tritylsulfanylmethyl)pyrrolidine-1,2-dicarboxylate
• 化学式: C₃₄H₄₁NO₄S
• 分子量: 559.77
• InChiKey: UTJBLMNWJWKEQW-XIJSCUBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-5-triphenylmethylthiomethyl-L-proline tert-butyl ester 在 三氟乙酸 作用下， 反应 1.0h， 以87%的产率得到trans-5-triphenylmethylthiomethyl-L-proline
  参考文献：
  名称：

  Efficient Microwave-Assisted Tandem N- to S-Acyl Transfer and Thioester Exchange for the Preparation of a Glycosylated Peptide Thioester

  摘要：

  A peptide carrying a mercaptomethylated proline derivative at the C-terminus was prepared by solid-phase peptide synthesis (SPPS) and converted to the thioester of 3-mercaptopropionic acid (MPA) by aqueous MPA under microwave irradiation conditions. This post-SPPS thioesterification reaction was successfully applied to the synthesis of a glycopeptide thioester composed of 25 amino acid (AA) residues, which was then used for the preparation of a 61-AA glycopeptide by the thioester condensation method.

  DOI：

  10.1021/ol0616034
• 作为产物：
  描述：

  t-butyl (2S,5RS)-N-t-butoxycarbonyl-5-methoxyprolinate 在 四氧化锇 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 N-甲基吲哚酮 、 水 、 碘 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 20.42h， 生成 N-tert-butoxycarbonyl-5-triphenylmethylthiomethyl-L-proline tert-butyl ester
  参考文献：
  名称：

  Efficient Microwave-Assisted Tandem N- to S-Acyl Transfer and Thioester Exchange for the Preparation of a Glycosylated Peptide Thioester

  摘要：

  A peptide carrying a mercaptomethylated proline derivative at the C-terminus was prepared by solid-phase peptide synthesis (SPPS) and converted to the thioester of 3-mercaptopropionic acid (MPA) by aqueous MPA under microwave irradiation conditions. This post-SPPS thioesterification reaction was successfully applied to the synthesis of a glycopeptide thioester composed of 25 amino acid (AA) residues, which was then used for the preparation of a 61-AA glycopeptide by the thioester condensation method.

  DOI：

  10.1021/ol0616034

文献信息

• Efficient Microwave-Assisted Tandem <i>N-</i> to <i>S</i>-Acyl Transfer and Thioester Exchange for the Preparation of a Glycosylated Peptide Thioester
  作者：Fumihiro Nagaike、Yuko Onuma、Chie Kanazawa、Hironobu Hojo、Akiharu Ueki、Yuko Nakahara、Yoshiaki Nakahara

  DOI：10.1021/ol0616034

  日期：2006.9.1

  A peptide carrying a mercaptomethylated proline derivative at the C-terminus was prepared by solid-phase peptide synthesis (SPPS) and converted to the thioester of 3-mercaptopropionic acid (MPA) by aqueous MPA under microwave irradiation conditions. This post-SPPS thioesterification reaction was successfully applied to the synthesis of a glycopeptide thioester composed of 25 amino acid (AA) residues, which was then used for the preparation of a 61-AA glycopeptide by the thioester condensation method.