N-propyl-N,N',N''-tri-Boc-guanidine | 217433-58-4

• 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-propyl-N,N',N''-tri-Boc-guanidine
• 英文别名: tert-butyl N-[N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-propan-2-ylcarbamate
• CAS: 217433-58-4
• 化学式: C₁₉H₃₅N₃O₆
• 分子量: 401.503
• InChiKey: ICNBBYIRPKYHBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoate 、 N-propyl-N,N',N''-tri-Boc-guanidine 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以64%的产率得到L-N-Cbz-ω-propyl-δ,ω,ω'-tri-Boc-arginine benzyl ester
  参考文献：
  名称：

  Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines:  New Reagents for Guanidinylation Reactions

  摘要：

  New guanidinylation reagents are reported. These reagents consist of N,N',N "-tri-Boc-guanidine (1) and N,N',N "-tri-Cbz-guanidine (2), which allow for the facile conversion of alcohols to substituted guanidines. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions,(1) to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents(2) N,N'-di-Boc-N "-triflylguanidine (3) and N,N'-di-Cbz-N "-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.

  DOI：

  10.1021/jo9814344
• 作为产物：
  描述：

  异丙醇 、 N,N′,N′′-三叔丁氧羰基胍 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以67%的产率得到N-propyl-N,N',N''-tri-Boc-guanidine
  参考文献：
  名称：

  Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines:  New Reagents for Guanidinylation Reactions

  摘要：

  New guanidinylation reagents are reported. These reagents consist of N,N',N "-tri-Boc-guanidine (1) and N,N',N "-tri-Cbz-guanidine (2), which allow for the facile conversion of alcohols to substituted guanidines. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions,(1) to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents(2) N,N'-di-Boc-N "-triflylguanidine (3) and N,N'-di-Cbz-N "-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.

  DOI：

  10.1021/jo9814344

文献信息

• Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines:  New Reagents for Guanidinylation Reactions
  作者：Konrad Feichtinger、Heather L. Sings、Tracy J. Baker、Kenneth Matthews、Murray Goodman

  DOI：10.1021/jo9814344

  日期：1998.11.1

  New guanidinylation reagents are reported. These reagents consist of N,N',N "-tri-Boc-guanidine (1) and N,N',N "-tri-Cbz-guanidine (2), which allow for the facile conversion of alcohols to substituted guanidines. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions,(1) to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents(2) N,N'-di-Boc-N "-triflylguanidine (3) and N,N'-di-Cbz-N "-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.