3,5-dideoxy-5-nitromethyl-D-xylono-1,4-lactone | 1220627-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,5-dideoxy-5-nitromethyl-D-xylono-1,4-lactone
• 英文别名: (3R,5R)-3-hydroxy-5-(2-nitroethyl)oxolan-2-one
• CAS: 1220627-38-2
• 化学式: C₆H₉NO₅
• 分子量: 175.141
• InChiKey: JDECBPWDOXBIPV-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 3,5-dideoxy-5-nitromethyl-D-xylono-1,4-lactone 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3,5-dideoxy-5-nitromethyl-2-O-trifluoromethanesulfonyl-D-xylono-1,4-lactone
  参考文献：
  名称：

  Studies on the stereocontrolled transformation of nitrohexofuranoses into 2-oxabicyclo[2.2.1]heptanes. V: Synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate

  摘要：

  The first total synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on an intramolecular cyclisation leading to 2-oxabicyclo[2 2 1]heptane derivatives It was observed that on of the substrate anomers produces an elimination rather than a cyclisation reaction These and other differences in the reaction paths for this key step were rationalised by means of molecular mechanism based Calculations. (c) 2010 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetasy.2009.12.018
• 作为产物：
  描述：

  3,5-dideoxy-1,2-O-isopropylidene-5-nitromethyl-α-D-xylofuranose 在 三氟乙酸 、 溴 、 barium carbonate 作用下， 以 水 、 1,4-二氧六环 为溶剂， 反应 55.0h， 以94%的产率得到3,5-dideoxy-5-nitromethyl-D-xylono-1,4-lactone
  参考文献：
  名称：

  Studies on the stereocontrolled transformation of nitrohexofuranoses into 2-oxabicyclo[2.2.1]heptanes. V: Synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate

  摘要：

  The first total synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on an intramolecular cyclisation leading to 2-oxabicyclo[2 2 1]heptane derivatives It was observed that on of the substrate anomers produces an elimination rather than a cyclisation reaction These and other differences in the reaction paths for this key step were rationalised by means of molecular mechanism based Calculations. (c) 2010 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetasy.2009.12.018