3,5-di-O-benzyl-6-deoxy-6-nitro-D-glucono-1,4-lactone | 528566-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-O-benzyl-6-deoxy-6-nitro-D-glucono-1,4-lactone
• 英文别名: (3R,4R,5R)-3-hydroxy-5-[(1R)-2-nitro-1-phenylmethoxyethyl]-4-phenylmethoxyoxolan-2-one
• CAS: 528566-62-3
• 化学式: C₂₀H₂₁NO₇
• 分子量: 387.389
• InChiKey: HGFOIHAGXADGPT-NCXUSEDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzyl-6-deoxy-6-nitro-D-glucono-1,4-lactone 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (1S,4S,5S,6R,7R)-6,7-bis(benzyloxy)-5-nitro-2-oxabicyclo[2.2.1]heptan-3-one
  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
• 作为产物：
  描述：

  6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 溴 、 三苯基膦 、 barium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 37.17h， 生成 3,5-di-O-benzyl-6-deoxy-6-nitro-D-glucono-1,4-lactone
  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. 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.
• 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.