(2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronic acid | 1252027-50-1

• 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: (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronic acid
• 英文别名: (2R,3R,4S,5S)-4,5-Bis(benzyloxy)-1-((benzyloxy)carbonyl)-3-hydroxypiperidine-2-carboxylic acid；(2R,3R,4S,5S)-3-hydroxy-4,5-bis(phenylmethoxy)-1-phenylmethoxycarbonylpiperidine-2-carboxylic acid
• CAS: 1252027-50-1
• 化学式: C₂₈H₂₉NO₇
• 分子量: 491.541
• InChiKey: GGDCFBDHTGLCIV-BKKFENPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105.53
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 四氢呋喃 、 水 、 异丙醇 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以79%的产率得到(2R,3R,4R,5S)-3,4,5-trihydroxypiperidine-2-carboxylic acid
  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：

  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 为溶剂， 反应 1.0h， 以97%的产率得到(2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronic acid
  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