(1S,3R,4S,5R,6S,7S)-3-(azidomethyl)-4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylic acid | 1170695-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4S,5R,6S,7S)-3-(azidomethyl)-4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylic acid
• 英文别名: (1S,3R,4S,5R,6S,7S)-3-(azidomethyl)-4,5-bis(phenylmethoxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylic acid
• CAS: 1170695-84-7
• 化学式: C₂₂H₂₃N₃O₅
• 分子量: 409.442
• InChiKey: YEDUKOOVMOLQQC-LJGAWZCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,3R,4S,5R,6S,7S)-3-(azidomethyl)-4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylic acid 、 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.08h， 以249 mg的产率得到(1S,3R,4S,5R,6S,7S)-ethyl 3-(((1S,3R,4S,5R,6S,7S)-3-(azidomethyl)-4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxamido)methyl)-4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylate
  参考文献：
  名称：

  Pyranocyclopropanyl sugar amino acids, a new class of constrained (di)peptide isosteres

  摘要：

  The design, synthesis and application of oxabicyclo[4.1.0]heptane amino acids as conformationally restricted sugar amino acid dipeptide isosteres are reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.009
• 作为产物：
  描述：

  (1S,3R,4S,5R,6S,7S)-ethyl 3-(azidomethyl)-4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以82%的产率得到(1S,3R,4S,5R,6S,7S)-3-(azidomethyl)-4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylic acid
  参考文献：
  名称：

  Pyranocyclopropanyl sugar amino acids, a new class of constrained (di)peptide isosteres

  摘要：

  The design, synthesis and application of oxabicyclo[4.1.0]heptane amino acids as conformationally restricted sugar amino acid dipeptide isosteres are reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.009

文献信息

• Sugar amino acid based peptide epoxyketones as potential proteasome inhibitors
  作者：Martijn D.P. Risseeuw、Bogdan I. Florea、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1016/j.bioorg.2010.04.004

  日期：2010.10

  This paper describes the synthesis and biological evaluation of nine epoxomicin-derived sugar amino acid containing peptide epoxyketones. The title compounds are assembled from six sugar amino acid dipeptide isosteres and are synthesized using solution-phase peptide synthesis protocols. Although neither of the compounds displays inhibitory activity towards any of the proteasome active sites, our approach holds promise towards the development of structurally new proteasome inhibitors. It is likely that the central sugar amino acid dipeptide isoster needs to be designed such that it closely resemble dipeptides at position P2 and P3 in proteasome substrates inhibitors, such as the Thr-Ile dipeptide present in the lead compound, epoxomicin. (C) 2010 Elsevier Inc. All rights reserved.
• Pyranocyclopropanyl sugar amino acids, a new class of constrained (di)peptide isosteres
  作者：Martijn D.P. Risseeuw、Gijs A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1016/j.tetasy.2009.03.009

  日期：2009.5

  The design, synthesis and application of oxabicyclo[4.1.0]heptane amino acids as conformationally restricted sugar amino acid dipeptide isosteres are reported. (C) 2009 Elsevier Ltd. All rights reserved.