benzyl (3S,5S,6R)-3-[1-(benzylamino)-3-[tert-butyl(dimethyl)silyl]oxypropyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate | 351020-28-5

• 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-[1-(benzylamino)-3-[tert-butyl(dimethyl)silyl]oxypropyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 351020-28-5
• 化学式: C₄₀H₄₈N₂O₅Si
• 分子量: 664.917
• InChiKey: SZPUAEXPUGUUQN-OLZNAMHDSA-N

物化性质

• 沸点：
  744.8±60.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (3S,5S,6R)-3-[1-(benzylamino)-3-[tert-butyl(dimethyl)silyl]oxypropyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate 在 偶氮二甲酸二异丙酯 、 氢氟酸 、 三乙胺 、 三苯基膦 、 mercury dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 (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：

  The asymmetric synthesis of (2 S ,3 R )-capreomycidine

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)00487-7
• 作为产物：
  描述：

  3-(叔丁基-二甲基-硅烷基OXY)-丙醛 在 aluminum oxide 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 1.42h， 生成 benzyl (3S,5S,6R)-3-[1-(benzylamino)-3-[tert-butyl(dimethyl)silyl]oxypropyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
  参考文献：
  名称：

  The asymmetric synthesis of (2 S ,3 R )-capreomycidine

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)00487-7

文献信息

• Asymmetric Synthesis of (2<i>S</i>,3<i>R</i>)-Capreomycidine and the Total Synthesis of Capreomycin IB
  作者：Duane E. DeMong、Robert M. Williams

  DOI：10.1021/ja0351241

  日期：2003.7.1

  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.
• 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.