tert-butyl N-[N'-[4-[[(2S)-2-[(2-bromoacetyl)amino]-4-methylpentanoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate | 350991-09-2

• 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: tert-butyl N-[N'-[4-[[(2S)-2-[(2-bromoacetyl)amino]-4-methylpentanoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 350991-09-2
• 化学式: C₂₃H₄₂BrN₅O₆
• 分子量: 564.52
• InChiKey: QYANQIQUKRTRRQ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[N'-[4-[[(2S)-2-[(2-bromoacetyl)amino]-4-methylpentanoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate 在 吡啶 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 Naphthalene-2-carboxylic acid {[(S)-1-(4-guanidino-butylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-{(S)-1-[(5-guanidino-pentylcarbamoyl)-methyl]-octyl}-amide
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Minalemine A, a Guanidine Peptide from the Marine Tunicate Didemnum rodriguesi

  摘要：

  The total synthesis of the 3S,2S and 3R,2S diastereomers (1a and 1b) of minalemine A and the identification of the natural compound as the 3R,2S isomer is described. The key step in the synthesis is the preparation of the two enantiomers of the beta -amino diacid 3-(N-carboxymethyl)-aminodecanoic acid (Ncma), which were obtained by stereoselective alkylation with allyl bromide of two nonanoic acid imides bearing chiral oxazolidinones as chiral auxiliaries. Natural minalemine A shows identical (1)H NMR and very similar (13)C NMR spectra compared to the two synthetic diastereomers. Sufficient differences in their chromatographic behavior to allow conclusive identification were not found. However, the corresponding N-2-naphthoyl amides presented quite distinct circular dichroism spectra (CD), and these confirmed the 3R,2S configuration for the natural minalemines and the R configuration for the constituent beta -amino diacid, Ncma.

  DOI：

  10.1021/jo010076t
• 作为产物：
  描述：

  N,N′-二-Boc-硫脲 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.17h， 生成 tert-butyl N-[N'-[4-[[(2S)-2-[(2-bromoacetyl)amino]-4-methylpentanoyl]amino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Minalemine A, a Guanidine Peptide from the Marine Tunicate Didemnum rodriguesi

  摘要：

  The total synthesis of the 3S,2S and 3R,2S diastereomers (1a and 1b) of minalemine A and the identification of the natural compound as the 3R,2S isomer is described. The key step in the synthesis is the preparation of the two enantiomers of the beta -amino diacid 3-(N-carboxymethyl)-aminodecanoic acid (Ncma), which were obtained by stereoselective alkylation with allyl bromide of two nonanoic acid imides bearing chiral oxazolidinones as chiral auxiliaries. Natural minalemine A shows identical (1)H NMR and very similar (13)C NMR spectra compared to the two synthetic diastereomers. Sufficient differences in their chromatographic behavior to allow conclusive identification were not found. However, the corresponding N-2-naphthoyl amides presented quite distinct circular dichroism spectra (CD), and these confirmed the 3R,2S configuration for the natural minalemines and the R configuration for the constituent beta -amino diacid, Ncma.

  DOI：

  10.1021/jo010076t