(1S,3R,4S,5S,6R,7R)-6,7-bis(benzyloxy)-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane | 528566-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4S,5S,6R,7R)-6,7-bis(benzyloxy)-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane
• 英文别名: (1S,3R,4S,5S,6R,7R)-6,7-dibenzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane；(1S,3R,4S,5S,6R,7R)-3-methoxy-5-nitro-6,7-bis(phenylmethoxy)-2-oxabicyclo[2.2.1]heptane
• CAS: 528566-68-9
• 化学式: C₂₁H₂₃NO₆
• 分子量: 385.417
• InChiKey: OOBAOXXDEPOFBD-MKUJHJDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,3R,4S,5S,6R,7R)-6,7-bis(benzyloxy)-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane 在 镍 氢气 、 碳酸氢钠 、 三氟乙酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 (1S,4S,5S,6R,7R)-[6,7-bis(benzyloxy)-3-hydroxy-2-oxabicyclo[2.2.1]hept-5-yl]carbamic acid benzyl ester
  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：

  (2R,3R,4S,5R)-4-(benzyloxy)-5-((R)-1-(benzyloxy)-2-nitroethyl)-2-methoxytetrahydrofuran-3-yl trifluoromethanesulfonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以0.12 g的产率得到(1S,3R,4S,5S,6R,7R)-6,7-bis(benzyloxy)-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane
  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

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.