(1S,4S,5S,6R,7R)-6,7-bis(benzyloxy)-5-nitro-2-oxabicyclo[2.2.1]heptan-3-one | 528566-63-4

• 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: (1S,4S,5S,6R,7R)-6,7-bis(benzyloxy)-5-nitro-2-oxabicyclo[2.2.1]heptan-3-one
• 英文别名: (1S,4S,5S,6R,7R)-6,7-dibenzyloxy-5-nitro-2-oxabicyclo[2.2.1]heptan-3-one；(1S,4S,5S,6R,7R)-5-nitro-6,7-bis(phenylmethoxy)-2-oxabicyclo[2.2.1]heptan-3-one
• CAS: 528566-63-4
• 化学式: C₂₀H₁₉NO₆
• 分子量: 369.374
• InChiKey: BHEFXJVOLRRAGK-QTMHVTGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,4S,5S,6R,7R)-6,7-bis(benzyloxy)-5-nitro-2-oxabicyclo[2.2.1]heptan-3-one 在 镍 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 生成 (1S,4S,5S,6R,7R)-5-amino-6,7-bis(benzyloxy)-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 吡啶 、 四丁基氟化铵 、 溴 、 三苯基膦 、 barium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 42.67h， 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

文献信息

• Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part VI: Synthesis and incorporation of the novel polyhydroxylated 5-aminocyclopent-1-enecarboxylic acids into peptides
  作者：Fernando Fernández、Begoña Pampín、Marcos A. González、Juan C. Estévez、Ramón J. Estévez

  DOI：10.1016/j.tetasy.2010.05.052

  日期：2010.8

  The first total synthesis of enantiopure methyl (3aR,4S,5S,6R,6aS)-4-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-5-carboxylate has been carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines. This approach is based on an intramolecular cyclization that leads to 2-oxabicyclo[2.2.1]heptane derivatives

  对映体纯的甲基（3a R，4 S，5 S，6 R，6a S）-4-苄氧基羰基氨基-6-羟基-2,2-二甲基-四氢-3a H-环戊基的第一个全合成[ d]] [1,3]二恶唑-5-羧酸酯已根据我们最近的新策略将硝基六氟呋喃糖酶转化为环戊胺而进行。该方法基于分子内环化，该环化导致了2-氧杂双环[2.2.1]庚烷衍生物。当尝试将这些β-氨基酸掺入肽时，观察到E1cb消除了甲氧基取代基。结果，开发了第一种多羟基化的5-氨基环戊-1-烯羧酸的合成方法和掺入到肽中的方法。
• 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.