N-methyl-N,N',N''-tri-Boc-guanidine | 216584-24-6

• 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-methyl-N,N',N''-tri-Boc-guanidine
• 英文别名: N-Methyl-N-,N'-,N"-Tri-Boc-Guanidine；tert-butyl N-[N,N'-bis[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-methylcarbamate
• CAS: 216584-24-6
• 化学式: C₁₇H₃₁N₃O₆
• 分子量: 373.45
• InChiKey: QYTWNVLIJLKOON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 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-methyl-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， 以87%的产率得到L-N-Cbz-ω-methyl-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：

  甲醇 、 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49%的产率得到N-methyl-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

• Guanidinylation reagents
  申请人：The Regents of The University of California

  公开号：US20030055214A1

  公开（公告）日：2003-03-20

  Trisubstituted N-protected guanidines and methods for use as guanidinylating reagents to yield N-protected guanidine derivatives.

  三取代N-保护胍和用作胍基化试剂的方法，以产生N-保护胍衍生物。
• GUANIDINYLATION REAGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0983232A2

  公开（公告）日：2000-03-08
• US6072075A
  申请人：——

  公开号：US6072075A

  公开（公告）日：2000-06-06
• US6380358B1
  申请人：——

  公开号：US6380358B1

  公开（公告）日：2002-04-30
• [EN] GUANIDINYLATION REAGENTS<br/>[FR] REACTIFS DE GUANIDINYLATION
  申请人：——

  公开号：WO1998052917A2

  公开（公告）日：1998-11-26

  [EN] Trisubstituted N-protected guanidines and methods for use as guanidinylating reagents to yield N-protected guanidine derivatives.
  [FR] La présente invention concerne des guanidines trisubstituées N-protégées et des procédés permettant d'utiliser ces dernières comme réactifs de guanidinylation afin d'obtenir des dérivés de guanidine N-protégés.