benzyl (3S,5S,6R)-3-[(1R)-1-[benzyl-[N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]-3-hydroxypropyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate | 351020-32-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: benzyl (3S,5S,6R)-3-[(1R)-1-[benzyl-[N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]-3-hydroxypropyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 351020-32-1
• 化学式: C₄₅H₅₂N₄O₉
• 分子量: 792.929
• InChiKey: KILHRFBCDXIJPN-FJFYJGPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  58
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl (3S,5S,6R)-3-[(1R)-1-[benzyl-[N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]-3-hydroxypropyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以88%的产率得到(3S,5S,6R)-3-{(R)-3-Benzyl-1-tert-butoxycarbonyl-2-[(Z)-tert-butoxycarbonylimino]-hexahydro-pyrimidin-4-yl}-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester
  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：

  N,N'-bis-Boc-S-methyl-isothiourea 在 氢氟酸 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.5h， 生成 benzyl (3S,5S,6R)-3-[(1R)-1-[benzyl-[N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]-3-hydroxypropyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
  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

文献信息

• The asymmetric synthesis of (2 S ,3 R )-capreomycidine
  作者：Duane E DeMong、Robert M Williams

  DOI：10.1016/s0040-4039(01)00487-7

  日期：2001.5

  An improved asymmetric synthesis of the guanidine-containing amino acid (2S,3R)-capreomycidine has been achieved in seven steps and 28% overall yield. The key synthetic step involved a Mannich-type reaction between a chiral glycine aluminum enolate and the benzyl-imine of 3-tert-butyldimethylsiloxy-propionaldehyde. (C) 2001 Elsevier Science Ltd. AH rights reserved.