5,6-anhydro-3-deoxy-1,2-O-isopropylidene-β-D-lyxo-hexofuranose | 457073-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-anhydro-3-deoxy-1,2-O-isopropylidene-β-D-lyxo-hexofuranose
• 英文别名: (3aR,5S,6aR)-2,2-dimethyl-5-(oxiran-2-yl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 457073-43-7
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: WKCVRECDMAIKJS-CZLDRYSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-anhydro-3-deoxy-1,2-O-isopropylidene-β-D-lyxo-hexofuranose 在 硫酸 作用下， 反应 2.0h， 生成 3-deoxy-L-lyxo-hexosa 、 (3R,5S,6S)-6-Hydroxymethyl-tetrahydro-pyran-2,3,5-triol
  参考文献：
  名称：

  合成含有肝素五糖的3-脱氧-L-艾杜糖醛酸，以探测抗凝血酶III结合序列的构象。

  摘要：

  我们在这项工作中报告了肝素的五糖活性位点的紧密类似物的完全合成，其中L-艾杜糖醛酸残基已在第三个位置脱氧。1H NMR研究表明，如预期的那样，这种修饰导致构象平衡向1C4转移（对构象平衡的贡献从37％上升至65％），并且对抗凝血酶III的亲和力大大降低（Kd 0.154 microM与0.050 microM）。

  DOI：

  10.1016/s0968-0896(98)00127-8
• 作为产物：
  描述：

  3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 sodium tetrahydroborate 、 potassium tert-butylate 、 溶剂黄146 、 nickel dichloride 、 叔丁醇 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 150.5h， 生成 5,6-anhydro-3-deoxy-1,2-O-isopropylidene-β-D-lyxo-hexofuranose
  参考文献：
  名称：

  合成含有肝素五糖的3-脱氧-L-艾杜糖醛酸，以探测抗凝血酶III结合序列的构象。

  摘要：

  我们在这项工作中报告了肝素的五糖活性位点的紧密类似物的完全合成，其中L-艾杜糖醛酸残基已在第三个位置脱氧。1H NMR研究表明，如预期的那样，这种修饰导致构象平衡向1C4转移（对构象平衡的贡献从37％上升至65％），并且对抗凝血酶III的亲和力大大降低（Kd 0.154 microM与0.050 microM）。

  DOI：

  10.1016/s0968-0896(98)00127-8

文献信息

• TOTAL SYNTHESIS OF GLUCOSEPANE AND COMPOUNDS OBTAINED THEREFROM
  申请人：YALE UNIVERSITY

  公开号：US20180291031A1

  公开（公告）日：2018-10-11

  Glucosepane is a structurally complex protein post-translational modification (PTM) believed to exist in all living organisms. Research in humans suggests that glucosepane plays a critical role in the pathophysiology of both diabetes and human aging; yet comprehensive biological investigations of this ‘metabolite have been’ greatly hindered by a scarcity of chemically homogeneous material available for study. Glucosepane possesses a unique chemical structure that incorporates a surprising, never-before-prepared non-aromatic tautomer of imidazole (hereafter termed an “iso-imidazole”), rendering it a challenging target for chemical synthesis. In this application, the inventors report the first total synthesis of glucosepane, enabled by the development of a novel one-pot method for preparation of the iso-imidazole core. The synthesis of the present invention is concise (8-steps starting from commercial materials), convergent, high-yielding (12% overall), and enantioselective. These results should prove useful to the art and practice of heterocyclic chemistry, and critical for the study of glucosepane and its role in human health and disease, especially the treatment of diabetic disorders or its impact on aging processes. Methods of synthesis, compounds obtained therefrom, pharmaceutical compositions and methods of treatment provide embodiments of the present invention.
• THE TOTAL SYNTHESIS OF GLUCOSEPANE AND RELATED CHEMICAL REACTIONS, COMPOUNDS AND COMPOSITIONS AND OBTAINED THEREFROM AND METHODS OF TREATMENT
  申请人：YALE UNIVERSITY

  公开号：US20200223860A1

  公开（公告）日：2020-07-16

  Glucosepane is a structurally complex protein post-translational modification (PTM) believed to exist in all living organisms. Research in humans suggests that glucosepane plays a critical role in the pathophysiology of both diabetes and human aging; yet comprehensive biological investigations of this metabolite have been greatly hindered by a scarcity of chemically homogeneous material available for study. Glucosepane possesses a unique chemical structure that incorporates a surprising, never-before-prepared non-aromatic tautomer of imidazole (hereafter termed an “iso-imidazole”), rendering it a challenging target for chemical synthesis. In this application, the inventors report the first total synthesis of glucosepane, enabled by the development of a novel one-pot method for preparation of the iso-imidazole core. The synthesis of the present invention is concise (8-steps starting from commercial materials), convergent, high-yielding (12% overall), and enantioselective. These results should prove useful to the art and practice of heterocyclic chemistry, and critical for the study of glucosepane and its role in human health and disease, especially the treatment of diabetic disorders or its impact on aging processes. Methods of synthesis, compounds obtained therefrom, pharmaceutical compositions and methods of treatment provide embodiments of the present invention.