3-(tert-butyldimethylsiloxy)-N-benzyl-propanaldimine | 121904-08-3

• 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: 3-(tert-butyldimethylsiloxy)-N-benzyl-propanaldimine
• 英文别名: N-benzyl-3-[tert-butyl(dimethyl)silyl]oxypropan-1-imine
• CAS: 121904-08-3
• 化学式: C₁₆H₂₇NOSi
• 分子量: 277.482
• InChiKey: CLLDZOHBLKALHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(tert-butyldimethylsiloxy)-N-benzyl-propanaldimine 在 三乙胺 、 mercury dichloride 、 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 benzyl (3S,5S,6R)-3-[(1R)-1-[benzyl-[(Z)-N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]-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
• 作为产物：
  描述：

  3-(叔丁基-二甲基-硅烷基OXY)-丙醛 、 苄胺 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以98%的产率得到3-(tert-butyldimethylsiloxy)-N-benzyl-propanaldimine
  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.