(S)-2-((1S,2S)-2-tert-Butoxycarbonylamino-1-carbamoyl-3-phenyl-propylamino)-4-methyl-pentanoic acid methyl ester | 158999-87-2

• 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: (S)-2-((1S,2S)-2-tert-Butoxycarbonylamino-1-carbamoyl-3-phenyl-propylamino)-4-methyl-pentanoic acid methyl ester
• 英文别名: methyl (2S)-2-[[(2S,3S)-1-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxo-4-phenylbutan-2-yl]amino]-4-methylpentanoate
• CAS: 158999-87-2
• 化学式: C₂₂H₃₅N₃O₅
• 分子量: 421.537
• InChiKey: ZDASOVMBSKVXRL-BZSNNMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-((1S,2S)-2-tert-Butoxycarbonylamino-1-carbamoyl-3-phenyl-propylamino)-4-methyl-pentanoic acid methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-2-((1S,2S)-2-Amino-1-carbamoyl-3-phenyl-propylamino)-4-methyl-pentanoic acid methyl ester
  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：

  Boc-PheψLeu-OMe 在 四丁基硫酸氢铵 sodium hydroxide 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以30%的产率得到(1'S,3R,5S)-3-<1'-<(tert-Butyloxycarbonyl)amino>-2'-phenylethyl>-5-isobutyl-2,6-dioxopiperazine
  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

• 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.