(2S,3S,4R,5S,6S)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid | 676241-07-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S,6S)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid
• 英文别名: (2S,3S,4R,5S,6S)-6-(azidomethyl)-3,4,5-tris(phenylmethoxy)oxane-2-carboxylic acid
• CAS: 676241-07-9
• 化学式: C₂₈H₂₉N₃O₆
• 分子量: 503.555
• InChiKey: PPNNTTJKEUAXKW-ZEEZOPKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6S)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid 在 diethylphosphoryl cyanide 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 92.0h， 生成 (2S,3S,4R,5S,6S)-6-{[((2S,3S,4R,5S,6S)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of pyranoid δ-sugar amino acids and their oligomers from per-benzylated β- C -vinyl glucoside

  摘要：

  Two pyranoid delta-sugar amino acids were prepared from the common per-benzylated beta-C-vinyl glucoside and easily oligomerised using solution-phase coupling methodology. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.032
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)ethene 在 sodium azide 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 乙酸酐 、 臭氧 、 三乙胺 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 149.5h， 生成 (2S,3S,4R,5S,6S)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of pyranoid δ-sugar amino acids and their oligomers from per-benzylated β- C -vinyl glucoside

  摘要：

  Two pyranoid delta-sugar amino acids were prepared from the common per-benzylated beta-C-vinyl glucoside and easily oligomerised using solution-phase coupling methodology. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.032

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.
• Synthesis of pyranoid δ-sugar amino acids and their oligomers from per-benzylated β- C -vinyl glucoside
  作者：François Durrat、Juan Xie、Jean-Marc Valéry

  DOI：10.1016/j.tetlet.2003.12.032

  日期：2004.2

  Two pyranoid delta-sugar amino acids were prepared from the common per-benzylated beta-C-vinyl glucoside and easily oligomerised using solution-phase coupling methodology. (C) 2003 Elsevier Ltd. All rights reserved.