tert-butyl [2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4-O-(1-naphthyl)methyl-L-iditol]uronate | 1252027-35-2

• 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: tert-butyl [2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4-O-(1-naphthyl)methyl-L-iditol]uronate
• 英文别名: 1-Benzyl 2-(tert-butyl) (2R,3R,4R,5S)-4,5-bis(benzyloxy)-3-(naphthalen-1-ylmethoxy)piperidine-1,2-dicarboxylate；1-O-benzyl 2-O-tert-butyl (2R,3R,4R,5S)-3-(naphthalen-1-ylmethoxy)-4,5-bis(phenylmethoxy)piperidine-1,2-dicarboxylate
• CAS: 1252027-35-2
• 化学式: C₄₃H₄₅NO₇
• 分子量: 687.833
• InChiKey: NTTMMWOMEWJRSS-BGFKDDMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.26
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl [2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4-O-(1-naphthyl)methyl-L-iditol]uronate 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以65%的产率得到tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate
  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：

  2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4-O-(1-naphthyl)methylene-L-iditol 、 叔丁醇 在 pyridinium dichromate 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以68%的产率得到tert-butyl [2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4-O-(1-naphthyl)methyl-L-iditol]uronate
  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