1-O-allyl-6-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3,4,5-tetra-O-benzyl-D-myo-inositol | 150772-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-allyl-6-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3,4,5-tetra-O-benzyl-D-myo-inositol
• CAS: 150772-58-0
• 化学式: C₅₀H₅₅N₃O₁₀
• 分子量: 858.001
• InChiKey: CWTXQKIGLLFIBV-AKTJAKEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  63.0
• 可旋转键数：
  22.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  163.06
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-O-allyl-6-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3,4,5-tetra-O-benzyl-D-myo-inositol 在 sodium methylate 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol
  参考文献：
  名称：

  A ready, convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein

  摘要：

  DOI：

  10.1021/ja00070a048
• 作为产物：
  描述：

  1-O-Allyl-2,3,4,5-O-tetrabenzyl-D-myo-inositol 在 sodium methylate 、 silver perchlorate 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 1-O-allyl-6-O-(2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3,4,5-tetra-O-benzyl-D-myo-inositol
  参考文献：
  名称：

  A ready, convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein

  摘要：

  DOI：

  10.1021/ja00070a048

文献信息

• Synthesis of the essential core of the human glycosylphosphatidylinositol (GPI) anchor
  作者：Barbara Richichi、Lucio Luzzatto、Rosario Notaro、Giancarlo la Marca、Cristina Nativi

  DOI：10.1016/j.bioorg.2010.12.002

  日期：2011.4

  role of GPI anchors is of paramount importance; however, we are still far from fully understanding the structure–function relationship of these molecules. One major limiting factor has been the tiny quantities available from natural sources; obtaining homogeneous and well-defined GPI structures by synthesis, is both a challenge and an attractive goal. We report here the convergent synthesis of the essential

  GPI锚的生物学作用至关重要。然而，我们离完全了解这些分子的结构-功能关系还很远。一个主要的限制因素是可从自然资源中获得的微量产品。通过合成获得均质且定义明确的GPI结构，既是挑战，也是诱人的目标。我们在这里报告人类GPI锚点1的基本核心的收敛合成，利用共同的前体获得三糖供体2和新的保护基序列。首次制备的最终产品具有生物活性。
• Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 6. Convergent Assembly of Subunits
  作者：Robert Madsen、Uko E. Udodong、Carmichael Roberts、David R. Mootoo、Peter Konradsson、Bert Fraser-Reid

  DOI：10.1021/ja00110a011

  日期：1995.2

  Glycophosphatidylinositol anchors of membrane-bound proteins are thought to comprise a common pentasaccharide core containing mannan, glucosamine, and inositol residues. A synthetic route to this core is described. In addition, the complete heptasaccharide moiety of the rat brain Thy-1 membrane anchor, the first mammalian membrane anchor to be characterized, has been synthesized. In the case of the Thy-1 anchor, the synthetic plan is based on three building blocks comprising glucosamine-inositol, galactosamine-mannose, and trimannan residues. Although glycosyl donors other than n-pentenyl glycosides (NPGs) have been used in preparing each of these building blocks, the final assembly of the heptasaccharide utilizes NPGs as the only glycosyl donors. The mildness of the conditions for these coupling reactions has allowed us to make provisions for subsequent installation of the three phosphodiester units.