methyl 4-C-[(3S,4R)-4-acetoxy-3-(methoxycarbonyl)-pyrrolidin-1-yl]methyl-3-O-benzyl-2-(benzyloxycarbonyl)-amino-6-O-tert-butyldimethylsilyl-2,4-dideoxy-α-D-glucopyranoside | 1248566-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-C-[(3S,4R)-4-acetoxy-3-(methoxycarbonyl)-pyrrolidin-1-yl]methyl-3-O-benzyl-2-(benzyloxycarbonyl)-amino-6-O-tert-butyldimethylsilyl-2,4-dideoxy-α-D-glucopyranoside
• CAS: 1248566-37-1
• 化学式: C₃₇H₅₄N₂O₁₀Si
• 分子量: 714.929
• InChiKey: YFSCKLLOCIIMMM-NAQICHAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  131.09
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 4-C-[(3S,4R)-4-acetoxy-3-(methoxycarbonyl)-pyrrolidin-1-yl]methyl-3-O-benzyl-2-(benzyloxycarbonyl)-amino-6-O-tert-butyldimethylsilyl-2,4-dideoxy-α-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 4.0h， 以79%的产率得到methyl 3-O-benzyl-2-O-(benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-2,4-dideoxy-4-C-[(3S,4R)-4-hydroxy-3-(methoxycarbonyl)pyrrolidin-1-yl]methyl-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 (3S,4R)-4-acetoxypyrrolidine-3-carboxylate 、 methyl 3-O-benzyl-2-N-(benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-2,4-dideoxy-4-C-formyl-α-D-glucopyranoside 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 1.5h， 以81%的产率得到methyl 4-C-[(3S,4R)-4-acetoxy-3-(methoxycarbonyl)-pyrrolidin-1-yl]methyl-3-O-benzyl-2-(benzyloxycarbonyl)-amino-6-O-tert-butyldimethylsilyl-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