tert-butyl N-[(2S)-3-hydroxy-1-oxo-1-[[(2S)-1-oxo-3-phenyl-1-(phenylmethoxyamino)propan-2-yl]amino]propan-2-yl]carbamate | 612815-61-9

• 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-[(2S)-3-hydroxy-1-oxo-1-[[(2S)-1-oxo-3-phenyl-1-(phenylmethoxyamino)propan-2-yl]amino]propan-2-yl]carbamate
• CAS: 612815-61-9
• 化学式: C₂₄H₃₁N₃O₆
• 分子量: 457.527
• InChiKey: QSWBXFXQVAZSIE-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  偶氮二甲酸二叔丁酯 、 tert-butyl N-[(2S)-3-hydroxy-1-oxo-1-[[(2S)-1-oxo-3-phenyl-1-(phenylmethoxyamino)propan-2-yl]amino]propan-2-yl]carbamate 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以28%的产率得到tert-butyl N-[(2-methylpropan-2-yl)oxycarbonylamino]-N-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-[[(2S)-1-oxo-3-phenyl-1-(phenylmethoxyamino)propan-2-yl]amino]propyl]carbamate
  参考文献：
  名称：

  Solid-Phase Synthesis of Conformationally Constrained Peptidomimetics Based on a 3,6-Disubstituted-1,4-diazepan-2,5-dione Core

  摘要：

  Starting from a Cl-trytyl linked hydroxylamine, a hydroxamic dipeptide having serine in the second position was prepared by using DMTMM as the coupling agent. Mitsunobu cyclization carried out under microwave heating gave very good yields of a 3,6-disubstituted-perhydro-diazepin-2,5-dione. This heterocycle can be used as a new platform for combinatorial chemistry or as a constraint to rigidify a small peptide.

  DOI：

  10.1021/jo034785d
• 作为产物：
  描述：

  (1-benzyloxycarbamoyl-2-phenylethyl)carbamic acid tert-butyl ester 在 N-甲基吗啉 、 三乙基硅烷 、 三氟乙酸 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 tert-butyl N-[(2S)-3-hydroxy-1-oxo-1-[[(2S)-1-oxo-3-phenyl-1-(phenylmethoxyamino)propan-2-yl]amino]propan-2-yl]carbamate
  参考文献：
  名称：

  Solid-Phase Synthesis of Conformationally Constrained Peptidomimetics Based on a 3,6-Disubstituted-1,4-diazepan-2,5-dione Core

  摘要：

  Starting from a Cl-trytyl linked hydroxylamine, a hydroxamic dipeptide having serine in the second position was prepared by using DMTMM as the coupling agent. Mitsunobu cyclization carried out under microwave heating gave very good yields of a 3,6-disubstituted-perhydro-diazepin-2,5-dione. This heterocycle can be used as a new platform for combinatorial chemistry or as a constraint to rigidify a small peptide.

  DOI：

  10.1021/jo034785d

文献信息

• Solid-Phase Synthesis of Conformationally Constrained Peptidomimetics Based on a 3,6-Disubstituted-1,4-diazepan-2,5-dione Core
  作者：Lucia Raffaella Lampariello、Daniela Piras、Manuela Rodriquez、Maurizio Taddei

  DOI：10.1021/jo034785d

  日期：2003.10.1

  Starting from a Cl-trytyl linked hydroxylamine, a hydroxamic dipeptide having serine in the second position was prepared by using DMTMM as the coupling agent. Mitsunobu cyclization carried out under microwave heating gave very good yields of a 3,6-disubstituted-perhydro-diazepin-2,5-dione. This heterocycle can be used as a new platform for combinatorial chemistry or as a constraint to rigidify a small peptide.