(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol] | 1252027-40-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol]
• CAS: 1252027-40-9
• 化学式: C₄₈H₅₂N₄O₁₀
• 分子量: 844.962
• InChiKey: COULYNAILWDGIP-VOUBYFBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  62.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  174.14
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol] 在 吡啶 、 1,3-丙二硫醇 、 三乙胺 作用下， 以 水 为溶剂， 反应 48.0h， 以81%的产率得到(2-amino-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol]
  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
• 作为产物：
  描述：

  (2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol] 在 hydrazinedithiocarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以92%的产率得到(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol]
  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