benzyl N-[2-oxo-2-[[(1S,4S,5S,6R,7R)-3-oxo-6,7-bis(phenylmethoxy)-2-oxabicyclo[2.2.1]heptan-5-yl]amino]ethyl]carbamate | 528566-64-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl N-[2-oxo-2-[[(1S,4S,5S,6R,7R)-3-oxo-6,7-bis(phenylmethoxy)-2-oxabicyclo[2.2.1]heptan-5-yl]amino]ethyl]carbamate
• CAS: 528566-64-5
• 化学式: C₃₀H₃₀N₂O₇
• 分子量: 530.577
• InChiKey: YZRGAJPYVUSZCY-NIDMROIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl N-[2-oxo-2-[[(1S,4S,5S,6R,7R)-3-oxo-6,7-bis(phenylmethoxy)-2-oxabicyclo[2.2.1]heptan-5-yl]amino]ethyl]carbamate 在 盐酸 、 亚硝酸特丁酯 、 一水合肼 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 生成
  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 镍 吡啶 、 四丁基氟化铵 、 氢气 、 溴 、 氯甲酸乙酯 、 三乙胺 、 三苯基膦 、 barium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 67.67h， 生成 benzyl N-[2-oxo-2-[[(1S,4S,5S,6R,7R)-3-oxo-6,7-bis(phenylmethoxy)-2-oxabicyclo[2.2.1]heptan-5-yl]amino]ethyl]carbamate
  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.