2-azido-1-O-benzoyl-2-deoxy-4,6-O-benzylidene-β-D-glucopyranose | 329038-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-azido-1-O-benzoyl-2-deoxy-4,6-O-benzylidene-β-D-glucopyranose
• 英文别名: 2-azido-2-deoxy-4,6-O-benzylidene-β-D-glucopyranosyl benzoate；2-azido-4,6-O-benzylidene-2-deoxyβ-D-glucopyranosyl benzoate；[(2R,4aR,6S,7R,8R,8aS)-7-azido-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl] benzoate
• CAS: 329038-46-2
• 化学式: C₂₀H₁₉N₃O₆
• 分子量: 397.387
• InChiKey: GCVLCGJLKSTICJ-HZLBELHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  2-azido-1-O-benzoyl-2-deoxy-4,6-O-benzylidene-β-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 methyl (2S,3S,4S,5R,6R)-6-[[(2R,4aR,6S,7R,8R,8aS)-7-acetamido-6-benzoyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3,4,5-triacetyloxyoxane-2-carboxylate
  参考文献：
  名称：

  各种 d-吡喃葡萄糖苷的区域选择性酯化：合成一个完全受保护的透明质酸二糖单元

  摘要：

  这里描述了各种 D-吡喃葡萄糖苷与三乙胺和酸酐的高区域选择性酯化反应，产率极好。它还强调了其在合成完全受保护的透明质酸二糖单元方面的应用。

  DOI：

  10.1055/s-2003-40338
• 作为产物：
  描述：

  2-azido-2-deoxy-1,3,4,6-tetra-O-trimethylsilyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 2-azido-1-O-benzoyl-2-deoxy-4,6-O-benzylidene-β-D-glucopyranose
  参考文献：
  名称：

  Regioselective One-Pot Protection of d-Glucosamine

  摘要：

  A highly regioselective one-pot transformation of 2-azido2-deoxy-1,3,4,6-tetra-O-trimethylsilyl-D-glucopyranose via sequential additions of various reagents was systematically studied, yielding the fully protected derivatives and the 1-, 3-, 4-, as well as 6-alcohols, respectively.

  DOI：

  10.1021/jo101320r

文献信息

• Synthesis of d-ribo-C18-phytosphingosine from d-glucosamine via the d-allosamine derivatives as key intermediates
  作者：Shun-Yuan Luo、Shankar R. Thopate、Ching-Yun Hsu、Shang-Cheng Hung

  DOI：10.1016/s0040-4039(02)00919-x

  日期：2002.7

  A straightforward synthesis of d-ribo-C18-phytosphingosine from d-glucosamine hydrochloride in ten steps in 18.4% overall yield via the d-allosamine derivatives as key intermediates is described here.

  本文描述了以10个步骤通过d-allosamine衍生物作为关键中间体从d-葡萄糖胺盐酸盐直接合成d-核糖基-C 18-植物鞘氨醇的方法，总收率为18.4％。
• Regioselective and stereoselective benzoylation of 2-N-protected 4,6-O-ketal derivatives of d-glucosamines with 1-(benzoyloxy)benzotriazole
  作者：Shang-Cheng Hung、Shankar R. Thopate、Cheng-Chung Wang

  DOI：10.1016/s0008-6215(00)00282-2

  日期：2001.1

  A highly regioelective and stereoselective benzoylation of the 2-N-protected 4,6-O-ketal derivatives of D-glucosamines with 1-(benzoyloxy)benzotriazole that affords the corresponding beta anomeric benzoates in excellent yields is described herein.

  本文描述了D-葡糖胺的2-N-保护的4，6-O-缩酮衍生物与1-（苯甲酰氧基）苯并三唑的高度区域选择性和立体选择性的苯甲酰化，其以优异的产率提供了相应的β-异头物苯甲酸酯。
• 1,6-Anhydro-β-<scp>l</scp>-hexopyranoses as Potent Synthons in the Synthesis of the Disaccharide Units of Bleomycin A₂ and Heparin
  作者：Shang-Cheng Hung、Shankar R. Thopate、Fa-Chen Chi、Shu-Wen Chang、Jinq-Chyi Lee、Cheng-Chung Wang、Yuh-Sheng Wen

  DOI：10.1021/ja003508a

  日期：2001.4.1
• Regioselective One-Pot Protection of <scp>d</scp>-Glucosamine
  作者：Ken-Lien Chang、Medel Manuel L. Zulueta、Xin-An Lu、Yong-Qing Zhong、Shang-Cheng Hung

  DOI：10.1021/jo101320r

  日期：2010.11.5

  A highly regioselective one-pot transformation of 2-azido2-deoxy-1,3,4,6-tetra-O-trimethylsilyl-D-glucopyranose via sequential additions of various reagents was systematically studied, yielding the fully protected derivatives and the 1-, 3-, 4-, as well as 6-alcohols, respectively.
• Regioselective Esterification of Various <scp>d</scp>-Glucopyranosides: Synthesis of a Fully Protected Disaccharide Unit of Hyaluronic Acid
  作者：Shang-Cheng Hung、Xin-An Lu、Chien-Hung Chou、Cheng-Chung Wang

  DOI：10.1055/s-2003-40338

  日期：——

  A highly regioselective esterification of various D-glucopyranosides with triethylamine and acid anhydrides in excellent yields is described here. Its application toward the synthesis of fully protected disaccharide unit of hyaluronic acid is also highlighted.

  这里描述了各种 D-吡喃葡萄糖苷与三乙胺和酸酐的高区域选择性酯化反应，产率极好。它还强调了其在合成完全受保护的透明质酸二糖单元方面的应用。