6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose | 848345-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose
• 英文别名: (3aR,5R,6S,6aR)-5-[(1S)-2-[tert-butyl(diphenyl)silyl]oxy-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 848345-27-7
• 化学式: C₂₅H₃₄O₆Si
• 分子量: 458.627
• InChiKey: DCTBRWUVYZAWMM-LHGONGGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose 在 吡啶 、 间苯三酚 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 、 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 183.0h， 生成 3,5-di-O-benzyl-6-deoxy-6-nitro-1,2-O-isopropylidene-β-L-idofuranose
  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：

  叔丁基二苯基氯硅烷 、 1,2-O-异亚丙基-beta-L-艾杜呋喃糖 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose
  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.