(R)-2-((R)-(tert-butoxycarbonylamino)(4-methoxyphenyl)methyl)pentanoic acid | 1200722-75-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-2-((R)-(tert-butoxycarbonylamino)(4-methoxyphenyl)methyl)pentanoic acid
• 英文别名: (2R)-2-[(R)-(4-methoxyphenyl)-[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pentanoic acid
• CAS: 1200722-75-3
• 化学式: C₁₈H₂₇NO₅
• 分子量: 337.416
• InChiKey: WITUTOXADKADFL-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-((R)-(tert-butoxycarbonylamino)(4-methoxyphenyl)methyl)pentanoic acid 、 L-丙氨酸甲酯盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以80%的产率得到(S)-methyl-2-((R)-2-((R)-(tert-butoxycarbonyl amino)(4-methoxyphenyl)methyl)pentanamido)propanoate
  参考文献：
  名称：

  An efficient synthetic approach towards trans-β2,3-amino acids and demonstration of their utility in the design of therapeutically important β2,3-peptides and α,β2,3-peptide aldehydes

  摘要：

  An efficient synthetic approach towards trans-beta(2,3)-amino acids involving anti-selective aldol, azidation and controlled hydrolysis as key steps is discussed. Apart from structural elaboration of these building blocks to homo- and hetero-dipeptides, possibility of selective endocyclic cleavage of the chiral auxiliary was advantageously used in the preparation of of alpha,beta-hybrid peptide alcohols and corresponding aldehydes, which are promising candidates for biological evaluation against proteases of therapeutic interest. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.072
• 作为产物：
  描述：

  tert-butyl (1R,2R)-2-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-1-(4-methoxyphenyl)pentylcarbamate 在 lithium hydroxide monohydrate 、 水 、 双氧水 、 potassium hydrogensulfate 作用下， 以 四氢呋喃 、 水 为溶剂， 以93%的产率得到(R)-2-((R)-(tert-butoxycarbonylamino)(4-methoxyphenyl)methyl)pentanoic acid
  参考文献：
  名称：

  An efficient synthetic approach towards trans-β2,3-amino acids and demonstration of their utility in the design of therapeutically important β2,3-peptides and α,β2,3-peptide aldehydes

  摘要：

  An efficient synthetic approach towards trans-beta(2,3)-amino acids involving anti-selective aldol, azidation and controlled hydrolysis as key steps is discussed. Apart from structural elaboration of these building blocks to homo- and hetero-dipeptides, possibility of selective endocyclic cleavage of the chiral auxiliary was advantageously used in the preparation of of alpha,beta-hybrid peptide alcohols and corresponding aldehydes, which are promising candidates for biological evaluation against proteases of therapeutic interest. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.072

文献信息

• An efficient synthetic approach towards trans-β2,3-amino acids and demonstration of their utility in the design of therapeutically important β2,3-peptides and α,β2,3-peptide aldehydes
  作者：Dhayalan Balamurugan、Kannoth M. Muraleedharan

  DOI：10.1016/j.tet.2009.09.072

  日期：2009.11

  An efficient synthetic approach towards trans-beta(2,3)-amino acids involving anti-selective aldol, azidation and controlled hydrolysis as key steps is discussed. Apart from structural elaboration of these building blocks to homo- and hetero-dipeptides, possibility of selective endocyclic cleavage of the chiral auxiliary was advantageously used in the preparation of of alpha,beta-hybrid peptide alcohols and corresponding aldehydes, which are promising candidates for biological evaluation against proteases of therapeutic interest. (C) 2009 Elsevier Ltd. All rights reserved.