(S)-4-benzyl-3-((R)-2-((S)-hydroxy(4-methoxyphenyl)methyl)pentanoyl)oxazolidin-2-one | 1200720-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-4-benzyl-3-((R)-2-((S)-hydroxy(4-methoxyphenyl)methyl)pentanoyl)oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(2R)-2-[(S)-hydroxy-(4-methoxyphenyl)methyl]pentanoyl]-1,3-oxazolidin-2-one
• CAS: 1200720-77-9
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: VICXFZQYUMSQGS-CEWLAPEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-((R)-2-((S)-hydroxy(4-methoxyphenyl)methyl)pentanoyl)oxazolidin-2-one 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到
  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：

  4-甲氧基苯甲醛 、 (S)-4-苄基-3-戊酰基噁唑烷-2-酮 在 三乙胺 、 magnesium chloride 、 三甲基氯硅烷 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以80%的产率得到(S)-4-benzyl-3-((R)-2-((S)-hydroxy(4-methoxyphenyl)methyl)pentanoyl)oxazolidin-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.