[(2S,3R,4S,5R)-2-methoxy-5-[(1R)-2-nitro-1-phenylmethoxyethyl]-4-phenylmethoxyoxolan-3-yl] trifluoromethanesulfonate | 1137111-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5R)-2-methoxy-5-[(1R)-2-nitro-1-phenylmethoxyethyl]-4-phenylmethoxyoxolan-3-yl] trifluoromethanesulfonate
• CAS: 1137111-83-1
• 化学式: C₂₂H₂₄F₃NO₉S
• 分子量: 535.495
• InChiKey: AUXHDMWJBHLDOT-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5R)-2-methoxy-5-[(1R)-2-nitro-1-phenylmethoxyethyl]-4-phenylmethoxyoxolan-3-yl] trifluoromethanesulfonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以0.17 g的产率得到(1S,3S,4S,5S,6R,7R)-6,7-dibenzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2008.12.017
• 作为产物：
  描述：

  三氟甲磺酸酐 、 methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-α-D-glucofuranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 [(2S,3R,4S,5R)-2-methoxy-5-[(1R)-2-nitro-1-phenylmethoxyethyl]-4-phenylmethoxyoxolan-3-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2008.12.017

文献信息

• 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.