tert-butyl N-[(1S,2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-1-cyano-3-phenylpropan-2-yl]carbamate | 159247-02-6

• 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: tert-butyl N-[(1S,2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-1-cyano-3-phenylpropan-2-yl]carbamate
• CAS: 159247-02-6
• 化学式: C₂₁H₃₂N₄O₃
• 分子量: 388.51
• InChiKey: FIHPQQZMOBWOKB-OKZBNKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S,2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-1-cyano-3-phenylpropan-2-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S)-2-[[(1S,2S)-2-amino-1-cyano-3-phenylpropyl]amino]-4-methylpentanamide
  参考文献：
  名称：

  A General Method for the Synthesis of Carbamoylmethyleneamino Pseudopeptides

  摘要：

  A general procedure for the preparation of (carbamoylmethylene)amino pseudopeptides from the corresponding (cyanomethylenene)amino analogues, compatible with peptide bonds and with the usual amino and carboxyl protecting groups, is described. This procedure involves the oxidative hydration of (cyanomethylene)amino pseudopeptides with basic hydrogen peroxide under phase-transfer conditions, using n-tetrabutylammonium hydrogen sulfate as catalyst. In the basic medium of this reaction the methyl esters of (carbamoylmethylene) amino pseudodipeptides cyclized to 2,6-dioxopiperazine analogues.

  DOI：

  10.1021/jo00092a019
• 作为产物：
  描述：

  亮氨酰胺 、 三甲基氰硅烷 、 N-Boc-L-苯丙氨醛 在 zinc(II) chloride 作用下， 以36%的产率得到tert-butyl N-[(1S,2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-1-cyano-3-phenylpropan-2-yl]carbamate
  参考文献：
  名称：

  A General Method for the Synthesis of Carbamoylmethyleneamino Pseudopeptides

  摘要：

  A general procedure for the preparation of (carbamoylmethylene)amino pseudopeptides from the corresponding (cyanomethylenene)amino analogues, compatible with peptide bonds and with the usual amino and carboxyl protecting groups, is described. This procedure involves the oxidative hydration of (cyanomethylene)amino pseudopeptides with basic hydrogen peroxide under phase-transfer conditions, using n-tetrabutylammonium hydrogen sulfate as catalyst. In the basic medium of this reaction the methyl esters of (carbamoylmethylene) amino pseudodipeptides cyclized to 2,6-dioxopiperazine analogues.

  DOI：

  10.1021/jo00092a019

文献信息

• C-Backbone branched peptides via reductive amination of cyanomethyleneamino pseudopeptides
  作者：Susana Herrero、M.Luisa Suárez-Gea、M.Teresa Garcı́a-López、Rosario Herranz

  DOI：10.1016/s0040-4039(02)00012-6

  日期：2002.2

  The synthesis of branched peptides from cyanomethylenamino pseudopeptides, via catalytic hydrogenation in the presence of amino acid derivatives, is described. When the inserted amino acid was a glycine derivative, the resulting branched peptide lactamized in situ to 2-oxopiperazine derivatives. This new C-backbone peptide branching approach is compatible with the diversity of amino acid side chains

  描述了由氰基亚甲基氨基伪肽通过在氨基酸衍生物存在下的催化氢化合成支链肽。当插入的氨基酸是甘氨酸衍生物时，所得的支链肽原位内酰胺化为2-氧代哌嗪衍生物。这种新的C骨干肽分支方法与氨基酸侧链的多样性兼容。
• Branched peptides and conformationally constrained analogues from cyanomethyleneamino pseudopeptides
  作者：M. Luisa Suárez-Gea、M. Teresa García-López、Rosario González-Muñiz、Susana Herrero、Rosario Herranz

  DOI：10.1016/0040-4039(96)00198-0

  日期：1996.3

  Catalytic hydrogenation of cyanomethyleneamino pseudopeptides, followed by peptide coupling and cyclization of the resulting aminomethyleneamino intermediates, gives access to branched and conformationally constrained peptide analogues.

  氰基亚甲基氨基假肽的催化加氢反应，然后进行肽偶联和所得氨基亚甲基氨基中间体的环化，可得到分支的且构象受限的肽类似物。
• A General Method for the Synthesis of Carbamoylmethyleneamino Pseudopeptides
  作者：M. Luisa Suarez-Gea、M. Teresa Garcia Lopez、Rosario Herranz

  DOI：10.1021/jo00092a019

  日期：1994.7

  A general procedure for the preparation of (carbamoylmethylene)amino pseudopeptides from the corresponding (cyanomethylenene)amino analogues, compatible with peptide bonds and with the usual amino and carboxyl protecting groups, is described. This procedure involves the oxidative hydration of (cyanomethylene)amino pseudopeptides with basic hydrogen peroxide under phase-transfer conditions, using n-tetrabutylammonium hydrogen sulfate as catalyst. In the basic medium of this reaction the methyl esters of (carbamoylmethylene) amino pseudodipeptides cyclized to 2,6-dioxopiperazine analogues.