methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-L-idofuranoside | 848345-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-L-idofuranoside
• CAS: 848345-36-8
• 化学式: C₂₁H₂₅NO₇
• 分子量: 403.432
• InChiKey: UFGQAIVJVXBWLG-XVCZEBDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  100.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-L-idofuranoside 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 (3R,5R,6S,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. Part 2: Synthesis of (1S,2R,3S,4S,5R)-3,4,5-trihydroxy-2-aminocyclopentanecarboxylic acid

  摘要：

  A recent 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 (1S,2R,3S,4S,5R)-2,3,4-trihydroxy-5-aminocyclopentanecarboxylic acid from L-idose. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.034
• 作为产物：
  描述：

  1,2-O-异亚丙基-beta-L-艾杜呋喃糖 在 吡啶 、 咪唑 、 间苯三酚 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 、 乙酰氯 、 sodium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 198.0h， 生成 methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-L-idofuranoside
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 2: Synthesis of (1S,2R,3S,4S,5R)-3,4,5-trihydroxy-2-aminocyclopentanecarboxylic acid

  摘要：

  A recent 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 (1S,2R,3S,4S,5R)-2,3,4-trihydroxy-5-aminocyclopentanecarboxylic acid from L-idose. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.034

文献信息

• Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 2: Synthesis of (1S,2R,3S,4S,5R)-3,4,5-trihydroxy-2-aminocyclopentanecarboxylic acid
  作者：Raquel G. Soengas、M. Begoña Pampı́n、Juan C. Estévez、Ramón J. Estévez

  DOI：10.1016/j.tetasy.2004.11.034

  日期：2005.1

  A recent 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 (1S,2R,3S,4S,5R)-2,3,4-trihydroxy-5-aminocyclopentanecarboxylic acid from L-idose. (C) 2004 Elsevier Ltd. All rights reserved.