(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->4)-[(1,5-dideoxy-1,5-imino-L-iditol)uronic acid] sodium salt | 1252027-15-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->4)-[(1,5-dideoxy-1,5-imino-L-iditol)uronic acid] sodium salt
• 英文别名: sodium;N-[(2S,3R,4R,5S,6R)-2-[(2R,3R,4R,5S)-2-carboxy-4,5-dihydroxypiperidin-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidate
• CAS: 1252027-15-8
• 化学式: C₁₄H₂₃N₂O₁₀*Na
• 分子量: 402.334
• InChiKey: WNNOLLLUHAJSBS-RDMJIWBOSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -9.24
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  204
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate] 在 三氟乙酸 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->4)-[(1,5-dideoxy-1,5-imino-L-iditol)uronic acid] sodium salt
  参考文献：
  名称：

  Synthesis of glycosaminoglycan oligosaccharides. Part 4: Synthesis of aza-l-iduronic acid-containing analogs of heparan sulfate oligosaccharides as heparanase inhibitors

  摘要：

  The synthesis of three azasugar-containing analogs of the disaccharide units of heparan sulfate, which are potential inhibitors of the enzyme heparanase, is reported. Synthetic routes were developed for the preparation of L-ido-nojirimycin type glycosyl acceptors with O-4 free. Glycosylation of these acceptors with an O-6 functionalized 2-azido-2-deoxy-n-glucose thioglycoside donor afforded the a-linked disaccharides in good yields. The advantages of using the 4-nitrobenzenesulfonyl group for the protection of the ring nitrogen of azasugars were demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.055