α-D-glucopyranosyl-(1-> 3)-N-(5-cyanopentyl)-1,5-dideoxy-1,5-imino-D-mannitol | 743427-28-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glucopyranosyl-(1-> 3)-N-(5-cyanopentyl)-1,5-dideoxy-1,5-imino-D-mannitol
• 英文别名: 6-[(2R,3R,4R,5R)-3,5-dihydroxy-2-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypiperidin-1-yl]hexanenitrile
• CAS: 743427-28-3
• 化学式: C₁₈H₃₂N₂O₉
• 分子量: 420.46
• InChiKey: UZULHEFAEODLIY-WVAGEOSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  α-D-glucopyranosyl-(1-> 3)-N-(5-cyanopentyl)-1,5-dideoxy-1,5-imino-D-mannitol 在 镍 氢气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以69%的产率得到α-D-glucopyranosyl-(1-> 3)-N-(6-aminohexyl)-1,5-dideoxy-1,5-imino-D-mannitol
  参考文献：
  名称：

  Golgi endomannosidase inhibitor, α-d-glucopyranosyl-(1→3)-1-deoxymannojirimycin: a five-step synthesis from maltulose and examples of N-modified derivatives

  摘要：

  Acid-catalysed O-acetylation of D-maltulose furnished the corresponding per-O-acetylated fructopyranose derivative that, after in situ deprotection at O-2 by reaction with triphenylphosphane dibromide, gave open-chain 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1-->4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose. Standard deprotection employing sodium methoxide in methanol at -30degreesC, followed by treatment of the resulting free 6-bromodeoxymaltulose with sodium azide in N,N-dimethylformamide, allowed access to 6-azidodeoxymaltulose. Hydrogenation over Pearlman's catalyst, accompanied by intramolecular reductive amination, yielded the desired title compound. This route allows access to preparative quantities and to a range of novel analogues with improved biostability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.015
• 作为产物：
  描述：

  α-D-glucopyranosyl-(1-> 4)-6-azido-6-deoxy-α/β-D-fructofuranose 在 palladium dihydroxide 氢气 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 α-D-glucopyranosyl-(1-> 3)-N-(5-cyanopentyl)-1,5-dideoxy-1,5-imino-D-mannitol
  参考文献：
  名称：

  Golgi endomannosidase inhibitor, α-d-glucopyranosyl-(1→3)-1-deoxymannojirimycin: a five-step synthesis from maltulose and examples of N-modified derivatives

  摘要：

  Acid-catalysed O-acetylation of D-maltulose furnished the corresponding per-O-acetylated fructopyranose derivative that, after in situ deprotection at O-2 by reaction with triphenylphosphane dibromide, gave open-chain 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1-->4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose. Standard deprotection employing sodium methoxide in methanol at -30degreesC, followed by treatment of the resulting free 6-bromodeoxymaltulose with sodium azide in N,N-dimethylformamide, allowed access to 6-azidodeoxymaltulose. Hydrogenation over Pearlman's catalyst, accompanied by intramolecular reductive amination, yielded the desired title compound. This route allows access to preparative quantities and to a range of novel analogues with improved biostability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.015

文献信息

• Golgi endomannosidase inhibitor, α-d-glucopyranosyl-(1→3)-1-deoxymannojirimycin: a five-step synthesis from maltulose and examples of N-modified derivatives
  作者：Josef Spreitz、Arnold E Stütz

  DOI：10.1016/j.carres.2004.04.015

  日期：2004.7

  Acid-catalysed O-acetylation of D-maltulose furnished the corresponding per-O-acetylated fructopyranose derivative that, after in situ deprotection at O-2 by reaction with triphenylphosphane dibromide, gave open-chain 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1-->4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose. Standard deprotection employing sodium methoxide in methanol at -30degreesC, followed by treatment of the resulting free 6-bromodeoxymaltulose with sodium azide in N,N-dimethylformamide, allowed access to 6-azidodeoxymaltulose. Hydrogenation over Pearlman's catalyst, accompanied by intramolecular reductive amination, yielded the desired title compound. This route allows access to preparative quantities and to a range of novel analogues with improved biostability. (C) 2004 Elsevier Ltd. All rights reserved.