N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4R,5S)-4,5-dihydroxy-2-(hydroxymethyl)piperidin-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide | 1253041-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4R,5S)-4,5-dihydroxy-2-(hydroxymethyl)piperidin-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1253041-15-4
• 化学式: C₁₄H₂₆N₂O₉
• 分子量: 366.368
• InChiKey: JXGDBZZZRYRMBX-WWSBIRTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  181
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[6-O-acetyl-3,4-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol] 在 甲醇 、 sodium methylate 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 120.0h， 以43%的产率得到N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4R,5S)-4,5-dihydroxy-2-(hydroxymethyl)piperidin-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
  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