N^α-CBz-DAPA-N^β-(N,N'-di-Boc-β-Lys)-OMe | 578710-41-5

• 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: N^α-CBz-DAPA-N^β-(N,N'-di-Boc-β-Lys)-OMe
• 英文别名: methyl (2S)-3-[[(3S)-3,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 578710-41-5
• 化学式: C₂₈H₄₄N₄O₉
• 分子量: 580.679
• InChiKey: QNGFAYOKBANGPD-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  41
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N^α-CBz-DAPA-N^β-(N,N'-di-Boc-β-Lys)-OMe 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到N^α-CBz-DAPA-N^β-(N,N'-di-Boc-β-Lys)-OH
  参考文献：
  名称：

  Asymmetric Synthesis of (2S,3R)-Capreomycidine and the Total Synthesis of Capreomycin IB

  摘要：

  A 27 step total synthesis of the tuberculostatic macrocyclic peptide antibiotic capreomycin 113 has been accomplished. The synthesis features the use of an enolate-aldimine condensation between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal as a means of preparing the cyclic guanidine amino acid (2S,3R)-capreomycidine. Additionally, a Hofmann rearrangement was exacted on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic acid residue.

  DOI：

  10.1021/ja0351241
• 作为产物：
  描述：

  3-氨基-N-(苄氧基羰基)-L-丙氨酸甲酯 、 bis(tert-butoxycarbonyl)-β-lysine N-hydroxysuccinimidyl ester 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到N^α-CBz-DAPA-N^β-(N,N'-di-Boc-β-Lys)-OMe
  参考文献：
  名称：

  Asymmetric Synthesis of (2S,3R)-Capreomycidine and the Total Synthesis of Capreomycin IB

  摘要：

  A 27 step total synthesis of the tuberculostatic macrocyclic peptide antibiotic capreomycin 113 has been accomplished. The synthesis features the use of an enolate-aldimine condensation between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal as a means of preparing the cyclic guanidine amino acid (2S,3R)-capreomycidine. Additionally, a Hofmann rearrangement was exacted on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic acid residue.

  DOI：

  10.1021/ja0351241