(S)-3-((R)-2-((R)-azido(4-methoxyphenyl)methyl)pentanoyl)-4-benzyloxazolidin-2-one | 1200721-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-3-((R)-2-((R)-azido(4-methoxyphenyl)methyl)pentanoyl)-4-benzyloxazolidin-2-one
• 英文别名: (4S)-3-[(2R)-2-[(R)-azido-(4-methoxyphenyl)methyl]pentanoyl]-4-benzyl-1,3-oxazolidin-2-one
• CAS: 1200721-70-5
• 化学式: C₂₃H₂₆N₄O₄
• 分子量: 422.484
• InChiKey: BTHVHGYXTUPTNV-TYPHKJRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (S)-3-((R)-2-((R)-azido(4-methoxyphenyl)methyl)pentanoyl)-4-benzyloxazolidin-2-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以94%的产率得到tert-butyl (1R,2R)-2-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-1-(4-methoxyphenyl)pentylcarbamate
  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：

  在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (S)-3-((R)-2-((S)-azido(4-methoxyphenyl)methyl)pentanoyl)-4-benzyloxazolidin-2-one 、 (S)-3-((R)-2-((R)-azido(4-methoxyphenyl)methyl)pentanoyl)-4-benzyloxazolidin-2-one
  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.