benzyl (3S,4R,5R)-4-[(2S,3R,4R,5S,6R)-3-azido-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-1-[[(2S,3S,4S,5R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-methoxy-4-phenylmethoxy-5-(phenylmethoxycarbonylamino)oxan-3-yl]methyl]-5-phenylmethoxypiperidine-3-carboxylate | 1248566-76-8

• 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: benzyl (3S,4R,5R)-4-[(2S,3R,4R,5S,6R)-3-azido-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-1-[[(2S,3S,4S,5R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-methoxy-4-phenylmethoxy-5-(phenylmethoxycarbonylamino)oxan-3-yl]methyl]-5-phenylmethoxypiperidine-3-carboxylate
• CAS: 1248566-76-8
• 化学式: C₆₉H₈₅N₅O₁₄Si
• 分子量: 1236.54
• InChiKey: QHCTWVAUULBFOJ-NYVFVVOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.09
• 重原子数：
  89
• 可旋转键数：
  31
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  186
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  benzyl (3S,4R,5R)-4-[(2S,3R,4R,5S,6R)-3-azido-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-1-[[(2S,3S,4S,5R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-methoxy-4-phenylmethoxy-5-(phenylmethoxycarbonylamino)oxan-3-yl]methyl]-5-phenylmethoxypiperidine-3-carboxylate 在 甲酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以91%的产率得到methyl 4-C-[(3R,4R,5S)-4-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-benzyloxy-5-benzyloxycarbonylpiperidin-1-ylmethyl]-3-O-benzyl-2-(benzyloxycarbonyl)-amino-2,4-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of novel azasugar-containing mimics of heparan sulfate fragments as potential heparanase inhibitors

  摘要：

  A series of eight novel, highly modified mono-, di- and trisaccharide derivatives, each containing an iminoalditol moiety, has been synthesized in the quest for potential heparanase inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.032
• 作为产物：
  描述：

  methyl 3-O-benzyl-2-N-(benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-2,4-dideoxy-4-C-formyl-α-D-glucopyranoside 、 benzyl (3R,4R,5S)-4-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)oxy-3-benzyloxy-piperidine-5-carboxylate 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以82%的产率得到benzyl (3S,4R,5R)-4-[(2S,3R,4R,5S,6R)-3-azido-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-1-[[(2S,3S,4S,5R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-methoxy-4-phenylmethoxy-5-(phenylmethoxycarbonylamino)oxan-3-yl]methyl]-5-phenylmethoxypiperidine-3-carboxylate
  参考文献：
  名称：

  Syntheses of novel azasugar-containing mimics of heparan sulfate fragments as potential heparanase inhibitors

  摘要：

  A series of eight novel, highly modified mono-, di- and trisaccharide derivatives, each containing an iminoalditol moiety, has been synthesized in the quest for potential heparanase inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.032