(3R,4R,5R)-1-butyl-5-(2-hydroxyethyl)piperidine-3,4-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4R,5R)-1-butyl-5-(2-hydroxyethyl)piperidine-3,4-diol
• 化学式: C₁₁H₂₃NO₃
• 分子量: 217.309
• InChiKey: GVWRNUVMCITDKC-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 四氧化锇 、 20% palladium hydroxide-activated charcoal 、 potassium tert-butylate 、 水 、 氢气 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 丙酮 、 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 34.5h， 生成 (3R,4R,5R)-1-butyl-5-(2-hydroxyethyl)piperidine-3,4-diol
  参考文献：
  名称：

  Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from d-mannitol derived nitroolefins

  摘要：

  The synthesis of isofagomine, epi-isofagomine and isofagomine analogues along with some new azasugars from two different vinyl nitro compounds, that were derived from D-mannitol, has been carried out. Two different synthetic strategies were followed for each of the vinyl-nitro precursors. Many of the azasugars synthesized showed inhibition in the micromolar range when tested against various glycosidase enzymes, opening up the possibility of modifying structural features for better and selective inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.021

文献信息

• Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from d-mannitol derived nitroolefins
  作者：Rashmi Roy、Pavan K. Kancharla、Y. Suman Reddy、Anita Brar、Y.D. Vankar

  DOI：10.1016/j.tetasy.2013.09.021

  日期：2013.12

  The synthesis of isofagomine, epi-isofagomine and isofagomine analogues along with some new azasugars from two different vinyl nitro compounds, that were derived from D-mannitol, has been carried out. Two different synthetic strategies were followed for each of the vinyl-nitro precursors. Many of the azasugars synthesized showed inhibition in the micromolar range when tested against various glycosidase enzymes, opening up the possibility of modifying structural features for better and selective inhibition. (C) 2013 Elsevier Ltd. All rights reserved.