methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-β-D-glucofuranoside | 528566-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-β-D-glucofuranoside
• 英文别名: (2R,3R,4R,5R)-2-methoxy-5-[(1R)-2-nitro-1-phenylmethoxyethyl]-4-phenylmethoxyoxolan-3-ol
• CAS: 528566-71-4
• 化学式: C₂₁H₂₅NO₇
• 分子量: 403.432
• InChiKey: UFGQAIVJVXBWLG-PFAUGDHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-β-D-glucofuranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2R,3R,4S,5R)-4-(benzyloxy)-5-((R)-1-(benzyloxy)-2-nitroethyl)-2-methoxytetrahydrofuran-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. III: synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate

  摘要：

  The first total synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on in intramolecular cyclization leading to 2-oxabicyclo[2.2.1] heptane derivatives. Differences in reactivity for this key step were rationalized by using molecular mechanism-based calculations. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.017
• 作为产物：
  描述：

  6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 乙酰氯 、 三苯基膦 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 56.17h， 生成 methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-β-D-glucofuranoside
  参考文献：
  名称：

  Stereocontrolled Transformation of Nitrohexofuranoses into Cyclopentylamines via 2-Oxabicyclo[2.2.1]heptanes:  Incorporation of Polyhydroxylated Carbocyclic β-Amino Acids into Peptides

  摘要：

  graphicA promising new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first total synthesis of a carbocyclic beta-amino acid and its incorporation into peptides. This strategy also afforded a new route to cyclopentylamines with well-known glycosidase inhibition properties.

  DOI：

  10.1021/ol034127f

文献信息

• Stereocontrolled Transformation of Nitrohexofuranoses into Cyclopentylamines via 2-Oxabicyclo[2.2.1]heptanes:  Incorporation of Polyhydroxylated Carbocyclic β-Amino Acids into Peptides
  作者：Raquel G. Soengas、Juan C. Estévez、Ramón J. Estévez

  DOI：10.1021/ol034127f

  日期：2003.5.1

  graphicA promising new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first total synthesis of a carbocyclic beta-amino acid and its incorporation into peptides. This strategy also afforded a new route to cyclopentylamines with well-known glycosidase inhibition properties.
• Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. III: synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate
  作者：Fernando Fernández、Juan C. Estévez、Fredy Sussman、Ramón J. Estévez

  DOI：10.1016/j.tetasy.2008.12.017

  日期：2008.12

  The first total synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on in intramolecular cyclization leading to 2-oxabicyclo[2.2.1] heptane derivatives. Differences in reactivity for this key step were rationalized by using molecular mechanism-based calculations. (C) 2008 Elsevier Ltd. All rights reserved.