methyl N'-(tert-butoxycarbonyl)-L-phenylalanyl-D-valinate | 876133-31-2

• 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: methyl N'-(tert-butoxycarbonyl)-L-phenylalanyl-D-valinate
• 英文别名: Boc-Phe-^DVal-OMe；Boc-Phe-D-Val-OMe；methyl (2R)-3-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]butanoate
• CAS: 876133-31-2
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: FBYKNRSPVRQRCS-JKSUJKDBSA-N

物化性质

• 沸点：
  540.9±50.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl N'-(tert-butoxycarbonyl)-L-phenylalanyl-D-valinate 在 sodium tetrahydroborate 、 四溴化碳 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 (S)-1-bromo-2-((S)-tert-butoxycarbonylphenylalanylamino)-3-methylbutane
  参考文献：
  名称：

  Higashiura, Kunihiko; Ienaga, Kazuharu, Journal of Chemical Research, Miniprint, 1992, p. 1901 - 1921

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-Phe-SH 在 碘 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 12.01h， 生成 methyl N'-(tert-butoxycarbonyl)-L-phenylalanyl-D-valinate
  参考文献：
  名称：

  Thioacetic Acid/NaSH-Mediated Synthesis of N-Protected Amino Thioacids and Their Utility in Peptide Synthesis

  摘要：

  Thioacids are recently gaining momentum due to their versatile reactivity. The reactivity of thioacids has been widely explored in the selective amide/peptide bond formation. Thioacids are generally synthesized from the reaction between activated carboxylic acids such as acid chlorides, active esters, etc., and Na2S, H2S, or NaSH. We sought to investigate whether the versatile reactivity of the thioacids can be tuned for the conversion of carboxylic acids into corresponding thioacids in the presence of NaSH. Herein, we report that thioacetic acid- and NaSH-mediated synthesis of N-protected amino thioacids from the corresponding N-protected amino acids, oxidative dimerization of thioacids, crystal conformations of thioacid oxidative dimers, and the utility of thioacids and oxidative dimers in peptide synthesis. Our results suggest that peptides can be synthesized without using standard coupling agents.

  DOI：

  10.1021/jo402872p

文献信息

• P(RNCH₂CH₂)₃N:  Efficient Catalysts for Transesterifications, Acylations, and Deacylations
  作者：Palanichamy Ilankumaran、J. G. Verkade

  DOI：10.1021/jo981819m

  日期：1999.4.1

  Extremely strong nonionic superbases of the type P(RNCH(2)CH(2))(3)N catalyze the transesterification of carboxylic acid esters with high selectivity and yields at 25 degrees C. These bases also catalyze the deacetylation of alcohols under mild conditions in quantitative yields. Using enol acetates as acylating agents, primary and secondary alcohols are efficiently protected as acetates through the

  P（RNCH（2）CH（2））（3）N类型的极强非离子超强碱催化羧酸酯的酯交换反应具有很高的选择性，并在25°C时产率较高。这些碱还催化在温和条件下醇的脱乙酰以定量的产量。使用烯醇乙酸酯作为酰化剂，伯和仲醇通过这些催化剂的作用被有效地保护为乙酸酯。在反应条件下可以耐受诸如环氧化物，氨基甲酸酯，乙缩醛，恶唑啉，硝基和炔基官能团的取代基。N保护的肽无需明显消旋就可以进行干净的酯交换反应，这使得该方法可能非常有用。
• Microwave-Assisted Synthesis of 2,5-Piperazinediones under Solvent-Free Conditions
  作者：J. Carlos Menéndez、Alberto López-Cobeñas、Pilar Cledera、J. Domingo Sánchez、Pilar López-Alvarado、M. Teresa Ramos、Carmen Avendaño

  DOI：10.1055/s-2005-918473

  日期：——

  A general, efficient and environmentally friendly procedure for the synthesis of 2,5-piperazinediones is described, involving the microwave irradiation of N-Boc dipeptide esters.

  描述了一种合成 2,5-哌嗪二酮的通用、高效和环保的方法，包括 N-Boc 二肽酯的微波辐射。
• Thioacetic Acid/NaSH-Mediated Synthesis of <i>N</i>-Protected Amino Thioacids and Their Utility in Peptide Synthesis
  作者：Sachitanand M. Mali、Hosahudya N. Gopi

  DOI：10.1021/jo402872p

  日期：2014.3.21

  Thioacids are recently gaining momentum due to their versatile reactivity. The reactivity of thioacids has been widely explored in the selective amide/peptide bond formation. Thioacids are generally synthesized from the reaction between activated carboxylic acids such as acid chlorides, active esters, etc., and Na2S, H2S, or NaSH. We sought to investigate whether the versatile reactivity of the thioacids can be tuned for the conversion of carboxylic acids into corresponding thioacids in the presence of NaSH. Herein, we report that thioacetic acid- and NaSH-mediated synthesis of N-protected amino thioacids from the corresponding N-protected amino acids, oxidative dimerization of thioacids, crystal conformations of thioacid oxidative dimers, and the utility of thioacids and oxidative dimers in peptide synthesis. Our results suggest that peptides can be synthesized without using standard coupling agents.
• Higashiura, Kunihiko; Ienaga, Kazuharu, Journal of Chemical Research, Miniprint, 1992, p. 1901 - 1921
  作者：Higashiura, Kunihiko、Ienaga, Kazuharu

  DOI：——

  日期：——