(2S,5R)-2-methoxy-5-(2-nitroethyl)-2,5-dihydrofurane | 1220627-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,5R)-2-methoxy-5-(2-nitroethyl)-2,5-dihydrofurane
• CAS: 1220627-43-9
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: KLEKRGZWSIKYNP-BQBZGAKWSA-N

反应信息

• 作为产物：
  描述：

  methyl 3,5-dideoxy-5-nitromethyl-2-O-trifluoromethanesulfonyl-D-xylofuranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以0.22 g的产率得到(3R,5S)-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane
  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