(S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-N-methoxy-N-methylpropanamide | 173259-61-5

• 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-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-N-methoxy-N-methylpropanamide
• 英文别名: benzyl N-[(2S)-1-[methoxy(methyl)amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxopropan-2-yl]carbamate
• CAS: 173259-61-5
• 化学式: C₁₈H₂₇N₃O₆
• 分子量: 381.429
• InChiKey: PNALDANAJSFICB-AWEZNQCLSA-N

物化性质

• 密度：
  1.180±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-N-methoxy-N-methylpropanamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ((S)-1-{(S)-1-[(S)-2-tert-Butoxycarbonylamino-1-(methoxy-methyl-carbamoyl)-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-3-methyl-butyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Tripeptide Aldehyde Inhibitors of Human Rhinovirus 3C Protease:  Design, Synthesis, Biological Evaluation, and Cocrystal Structure Solution of P₁ Glutamine Isosteric Replacements

  摘要：

  The investigation of tripeptide aldehydes as reversible covalent inhibitors of human rhinovirus (HRV) 3C protease (3CP) is reported. Molecular models based on the apo crystal structure of HRV-14 3CP and other trypsin-like serine proteases were constructed to approximate the binding of peptide substrates, generate transition state models of P-1-P-1' amide cleavage, and propose novel tripeptide aldehydes. Glutaminal derivatives have limitations since they exist predominantly in the cyclic hemiaminal form. Therefore, several isosteric replacements for the P-1 carboxamide side chain were designed and incorporated into the tripeptide aldehydes. These compounds were found to be potent inhibitors of purified HRV-14 3CP with K(i)s ranging from 0.005 to 0.64 mu M. Several have low micromolar antiviral activity when tested against HRV-14-infected H1-HeLa cells. The N-acetyl derivative 3 was also shown to be active against HRV serotypes 2, 16, and 89. High-resolution cocrystal structures of HRV-8 3CP, covalently bound to compounds 3, 15, and 16, were solved. These cocrystal structures were analyzed and compared with our original HRV-14 3CP-substrate and inhibitor models.

  DOI：

  10.1021/jm980071x
• 作为产物：
  描述：

  3-氨基-N-Cbz-L-丙氨酸 在 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 10.25h， 生成 (S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-N-methoxy-N-methylpropanamide
  参考文献：
  名称：

  氨基苯甲酸-1-磷酸膦酰胺的磷酰胺类似物的合成

  摘要：

  磷酰胺衍生物13和15被制备为1磷酸Sphinganine的类似物（4）。合成的关键步骤是二氨基丙酸7的N-甲氧基-N-甲基羧酰胺的烷基化和随后还原中间形成的酮8，得到非对映体醇9。9的脱保护和磷酸化导致期望的产物13和15。

  DOI：

  10.1016/0040-4020(95)01119-6

文献信息

• Synthesis of Crystalline Orthogonally N-Protected (S)- or (R)-2,3-Diaminopropionaldehyde from L- or D-Aspartic Acid
  作者：Daniel Schirlin、Jean-Michel Altenburger

  DOI：10.1055/s-1995-4111

  日期：1995.11

  Procedures are described for the easy preparation of crystalline orthogonally N-protected (S)- or (R)-2,3-diaminopropionaldehyde of high optical purity from L- or D-aspartic acid, respectively, and in reasonable yields.

  本文描述了一种从L-或D-天冬氨酸中简单制备高光学纯度的正交N保护的(S)-或(R)-2,3-二氨基丙醛的方法，且产率合理。