(1S,3R,4S,5S,6R,7R)-[6,7-bis(benzyloxy)-3-methoxy-2-oxabicyclo[2.2.1]hept-5-yl]carbamic acid benzyl ester | 528566-69-0

• 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-2-oxabicyclo[2.2.1]hept-5-yl]carbamic acid benzyl ester
• 英文别名: benzyl N-[(1S,3R,4S,5S,6R,7R)-3-methoxy-6,7-bis(phenylmethoxy)-2-oxabicyclo[2.2.1]heptan-5-yl]carbamate
• CAS: 528566-69-0
• 化学式: C₂₉H₃₁NO₆
• 分子量: 489.568
• InChiKey: GQTLPLJDUVNNFV-WBKISLEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 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-2-oxabicyclo[2.2.1]hept-5-yl]carbamic acid benzyl ester 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 ((1S,2R,3S,4R,5R)-2,4-Bis-benzyloxy-3-hydroxy-5-hydroxymethyl-cyclopentyl)-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：

  (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 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 22.0h， 生成 (1S,3R,4S,5S,6R,7R)-[6,7-bis(benzyloxy)-3-methoxy-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

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.