α-D-glucopyranosyl-(1-> 3)-1,5-dideoxy-1,5-imino-D-mannitol | 153154-53-1

• 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)-1,5-dideoxy-1,5-imino-D-mannitol
• 英文别名: 1,5-dideoxy-3-O-(α-D-glucopyranosyl)-1,5-imino-D-mannitol；1-deoxy-3-O-(α-D-glucopyranosyl)-mannojirimycin；a-D-Glucopyranosyl-(1->3)-1-deoxymannojirimycin；(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R)-3,5-dihydroxy-2-(hydroxymethyl)piperidin-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 153154-53-1
• 化学式: C₁₂H₂₃NO₉
• 分子量: 325.316
• InChiKey: KCJQDMHUYOITFI-BBFNFCGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  172
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  α-D-glucopyranosyl-(1-> 3)-1,5-dideoxy-1,5-imino-D-mannitol 在 镍 氢气 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、5.0 MPa 条件下， 反应 142.0h， 生成 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：

  2,4-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol 在 钯 咪唑 、 2,4,6-三甲基吡啶 、 盐酸 、 3 A molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 388.25h， 生成 α-D-glucopyranosyl-(1-> 3)-1,5-dideoxy-1,5-imino-D-mannitol
  参考文献：
  名称：

  Synthesis of 1,5-dideoxy-3-O-(α-D-mannopyranosyl)-1,5-imino-D-mannitol and 1,5-dideoxy-3-O-(α-D-glucopyranosyl)-1,5-imino-D-mannitol: Powerful inhibitors of endomannosidase

  摘要：

  The synthesis and conformations of 3-O-methylDMJ, 3-O-(alpha-D-glucopyranosyl)-DMJ (Glcalpha1,3DMJ), and 3-O-(alpha-D-mannopyranosyl)-DMJ (Manalpha1,3DMJ) are described. Manalpha1,3DMJ and Glcalpha1,3DMJ are shown to be very powerful inhibitors of an endomannosidase. The potential use of these compounds in both probing the pathways of N-linked glycoprotein processing and in the chemotherapy of some viral diseases is discussed.

  DOI：

  10.1016/s0957-4166(00)82250-8

文献信息

• Synthesis of 1,5-dideoxy-3-O-(α-D-mannopyranosyl)-1,5-imino-D-mannitol and 1,5-dideoxy-3-O-(α-D-glucopyranosyl)-1,5-imino-D-mannitol: Powerful inhibitors of endomannosidase
  作者：Helen Ardron、Terry D. Butters、Frances M. Platt、Mark R. Wormald、Raymond A Dwek、George W.J. Fleet、Gary S. Jacob

  DOI：10.1016/s0957-4166(00)82250-8

  日期：1993.1

  The synthesis and conformations of 3-O-methylDMJ, 3-O-(alpha-D-glucopyranosyl)-DMJ (Glcalpha1,3DMJ), and 3-O-(alpha-D-mannopyranosyl)-DMJ (Manalpha1,3DMJ) are described. Manalpha1,3DMJ and Glcalpha1,3DMJ are shown to be very powerful inhibitors of an endomannosidase. The potential use of these compounds in both probing the pathways of N-linked glycoprotein processing and in the chemotherapy of some viral diseases is discussed.
• 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.