[(2R,3R,4R,6R)-4-azido-3-hydroxy-6-phenylsulfanyloxan-2-yl]methyl 3-methylbutanoate | 1239701-21-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: [(2R,3R,4R,6R)-4-azido-3-hydroxy-6-phenylsulfanyloxan-2-yl]methyl 3-methylbutanoate
• CAS: 1239701-21-3
• 化学式: C₁₇H₂₃N₃O₄S
• 分子量: 365.453
• InChiKey: VIPDOZPYKGKVML-MUIFIZLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,6R)-4-azido-3-hydroxy-6-phenylsulfanyloxan-2-yl]methyl 3-methylbutanoate 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of functionalized trisaccharides as p53-peptide mimics

  摘要：

  Oligosaccharides represent potentially useful scaffolds for the development of peptidomimetics. We report here the design and synthesis of functionalized trisaccharides modeled after an alpha-helical 15-mer peptide region of p53 which binds to its cellular regulator MDM2. The trisaccharide scaffold was obtained efficiently by applying the sulfoxide glycosylation reaction as a key methodology. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.012
• 作为产物：
  描述：

  (2R,3R,4R,6R)-4-azido-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-ol 、 异戊酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到[(2R,3R,4R,6R)-4-azido-3-hydroxy-6-phenylsulfanyloxan-2-yl]methyl 3-methylbutanoate
  参考文献：
  名称：

  Design and synthesis of functionalized trisaccharides as p53-peptide mimics

  摘要：

  Oligosaccharides represent potentially useful scaffolds for the development of peptidomimetics. We report here the design and synthesis of functionalized trisaccharides modeled after an alpha-helical 15-mer peptide region of p53 which binds to its cellular regulator MDM2. The trisaccharide scaffold was obtained efficiently by applying the sulfoxide glycosylation reaction as a key methodology. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.012

文献信息

• Design and synthesis of functionalized trisaccharides as p53-peptide mimics
  作者：Kaori Sakurai、Daniel Kahne

  DOI：10.1016/j.tetlet.2010.05.012

  日期：2010.7

  Oligosaccharides represent potentially useful scaffolds for the development of peptidomimetics. We report here the design and synthesis of functionalized trisaccharides modeled after an alpha-helical 15-mer peptide region of p53 which binds to its cellular regulator MDM2. The trisaccharide scaffold was obtained efficiently by applying the sulfoxide glycosylation reaction as a key methodology. (C) 2010 Elsevier Ltd. All rights reserved.