2-((S)-1-Amino-5-benzyloxycarbonylamino-pentyl)-oxazole-4-carboxylic acid | 301662-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((S)-1-Amino-5-benzyloxycarbonylamino-pentyl)-oxazole-4-carboxylic acid
• 英文别名: 2-[(1S)-1-amino-5-(phenylmethoxycarbonylamino)pentyl]-1,3-oxazole-4-carboxylic acid
• CAS: 301662-82-8
• 化学式: C₁₇H₂₁N₃O₅
• 分子量: 347.371
• InChiKey: WLWKFWZFWZTMKU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((S)-1-Amino-5-benzyloxycarbonylamino-pentyl)-oxazole-4-carboxylic acid 在 二苯基磷酸 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 以19%的产率得到benzyl N-[4-[(4S,11S,18S)-2,9,16-trioxo-11,18-bis[4-(phenylmethoxycarbonylamino)butyl]-6,13,20-trioxa-3,10,17,22,23,24-hexazatetracyclo[17.2.1.15,8.112,15]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaen-4-yl]butyl]carbamate
  参考文献：
  名称：

  Functionalized platforms based on marine cyclopeptides: different pathways to the hexapeptide

  摘要：

  The synthesis of macrocyclic, roughly planar, exclusively syn-functionalized hexapeptides, related to dolastatin I and bistratamide C from enantiomerically pure oxazole precursors is reported. The platforms can either be synthesized in a stepwise procedure by final cyclization of the linear oxazole trimers or in a direct 'one-pot' reaction. The investigation on the coupling of these building blocks into linear dimers and trimers with modern peptide coupling reagents is reported. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01057-1
• 作为产物：
  描述：

  Boc-Lys(Z)-Ser-OMe 在 lithium hydroxide 、 二乙胺基三氟化硫 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 2-((S)-1-Amino-5-benzyloxycarbonylamino-pentyl)-oxazole-4-carboxylic acid
  参考文献：
  名称：

  Regioselective Synthesis of Antiparallel Loops on a Macrocyclic Scaffold Constrained by Oxazoles and Thiazoles

  摘要：

  [GRAPHICS]The regioselective syntheses and structures are reported for two tris-macrocylic compounds, each possessing two antiparallel loops on a macrocyclic scaffold constrained by two oxazoles and two thiazoles. NMR solution structures show the loops projecting from the same face of the macrocycle. Such molecules are shown to be prototypes for mimicking multiple loops of proteins.

  DOI：

  10.1021/ol026463m

文献信息

• Regioselective Synthesis of Antiparallel Loops on a Macrocyclic Scaffold Constrained by Oxazoles and Thiazoles
  作者：Yogendra Singh、Martin J. Stoermer、Andrew J. Lucke、Matthew P. Glenn、David P. Fairlie

  DOI：10.1021/ol026463m

  日期：2002.10.1

  [GRAPHICS]The regioselective syntheses and structures are reported for two tris-macrocylic compounds, each possessing two antiparallel loops on a macrocyclic scaffold constrained by two oxazoles and two thiazoles. NMR solution structures show the loops projecting from the same face of the macrocycle. Such molecules are shown to be prototypes for mimicking multiple loops of proteins.
• Functionalized platforms based on marine cyclopeptides: different pathways to the hexapeptide
  作者：Christoph Boss、Palle H Rasmussen、Alexander R Wartini、Siegfried R Waldvogel

  DOI：10.1016/s0040-4039(00)01057-1

  日期：2000.8

  The synthesis of macrocyclic, roughly planar, exclusively syn-functionalized hexapeptides, related to dolastatin I and bistratamide C from enantiomerically pure oxazole precursors is reported. The platforms can either be synthesized in a stepwise procedure by final cyclization of the linear oxazole trimers or in a direct 'one-pot' reaction. The investigation on the coupling of these building blocks into linear dimers and trimers with modern peptide coupling reagents is reported. (C) 2000 Published by Elsevier Science Ltd.