Z-Trp-Pro-OTmsi | 702702-46-3

• 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: Z-Trp-Pro-OTmsi
• 英文别名: 1-trimethylsilylpropan-2-yl (2S)-1-[(2S)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylate
• CAS: 702702-46-3
• 化学式: C₃₀H₃₉N₃O₅Si
• 分子量: 549.742
• InChiKey: LTWFCEOZHHMSOH-KFTXQHHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Trp-Pro-OTmsi 在 palladium on activated charcoal N-甲基吡咯烷酮 、 水 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 H-Trp-Pro-OTmsi
  参考文献：
  名称：

  Application of substituted 2-(trimethylsilyl)ethyl esters to suppress diketopiperazine formation

  摘要：

  The use of differently substituted 2-(trimethylsilyl)ethyl esters for C-terminal protection in peptide synthesis has been investigated. While the use of the unsubstituted 2-(trimethylsilyl)ethyl ester resulted in a substantial amount of diketopiperazine at the dipeptide stage, use of the corresponding methyl-substituted silyl ester gave a significant reduction of this undesired pathway. Both esters could be deprotected by fluoride-induced cleavage under mild conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.054
• 作为产物：
  描述：

  三甲基甲硅烷基-2-羟基丙烷 在 palladium on activated charcoal N-甲基吗啉 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 生成 Z-Trp-Pro-OTmsi
  参考文献：
  名称：

  Application of substituted 2-(trimethylsilyl)ethyl esters to suppress diketopiperazine formation

  摘要：

  The use of differently substituted 2-(trimethylsilyl)ethyl esters for C-terminal protection in peptide synthesis has been investigated. While the use of the unsubstituted 2-(trimethylsilyl)ethyl ester resulted in a substantial amount of diketopiperazine at the dipeptide stage, use of the corresponding methyl-substituted silyl ester gave a significant reduction of this undesired pathway. Both esters could be deprotected by fluoride-induced cleavage under mild conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.054

文献信息

• Application of substituted 2-(trimethylsilyl)ethyl esters to suppress diketopiperazine formation
  作者：Katarzyna Borsuk、Floris L van Delft、Ivo F Eggen、Paul B.W ten Kortenaar、Annet Petersen、Floris P.J.T Rutjes

  DOI：10.1016/j.tetlet.2004.03.054

  日期：2004.4

  The use of differently substituted 2-(trimethylsilyl)ethyl esters for C-terminal protection in peptide synthesis has been investigated. While the use of the unsubstituted 2-(trimethylsilyl)ethyl ester resulted in a substantial amount of diketopiperazine at the dipeptide stage, use of the corresponding methyl-substituted silyl ester gave a significant reduction of this undesired pathway. Both esters could be deprotected by fluoride-induced cleavage under mild conditions. (C) 2004 Elsevier Ltd. All rights reserved.