((3aR,4R,6R,6aR)-6-(4-carbamoyl-5-hydroxy-1H-imidazol-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetate | 168906-86-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: ((3aR,4R,6R,6aR)-6-(4-carbamoyl-5-hydroxy-1H-imidazol-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetate
• CAS: 168906-86-3
• 化学式: C₁₄H₁₉N₃O₇
• 分子量: 341.321
• InChiKey: USEGGROYIBUBJZ-QYVSTXNMSA-N

物化性质

• 沸点：
  601.1±55.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  135.13
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ((3aR,4R,6R,6aR)-6-(4-carbamoyl-5-hydroxy-1H-imidazol-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetate 在 水 、 三氟乙酸 作用下， 反应 3.0h， 以61%的产率得到咪唑立宾
  参考文献：
  名称：

  A synthesis of bredinin (Mizoribine®) from an acyclic precursor

  摘要：

  Bredinin (4-carbamoyl-1-beta-D-ribofuranosylimidazolium-5-olate, 1) was synthesised by the formation of a malonamate from 2,3-isopropylidene-D-ribofuranosylamine and ethyl malonyl chloride, followed by a sequence involving amination, via reduction of an oxime, heterocycle formation and then deprotection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.085
• 作为产物：
  描述：

  2-amino-N-(5-O-acetyl-2,3-O-isopropylidene-D-ribofuranosyl)malondiamide 、 甲亚胺乙酯盐酸盐 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以69%的产率得到((3aR,4R,6R,6aR)-6-(4-carbamoyl-5-hydroxy-1H-imidazol-1-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetate
  参考文献：
  名称：

  A synthesis of bredinin (Mizoribine®) from an acyclic precursor

  摘要：

  Bredinin (4-carbamoyl-1-beta-D-ribofuranosylimidazolium-5-olate, 1) was synthesised by the formation of a malonamate from 2,3-isopropylidene-D-ribofuranosylamine and ethyl malonyl chloride, followed by a sequence involving amination, via reduction of an oxime, heterocycle formation and then deprotection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.085

文献信息

• A Novel Synthesis of Mizoribine® and Related Nucleosides from Acyclic Precursors
  作者：David Ewing、Robert Humble、Grahame Mackenzie、Gordon Shaw

  DOI：10.1080/15257779508012385

  日期：1995.5.1

  Mizoribine(R) (4-carbamoyl-1-beta-D-ribofuranosylimidazolium-5-olate)(13 beta) and its 4-cyano analogue (20) were synthesized by formation of a malonamide from 2,3-isopropylidene-D-ribosylamine and a malonic acid derivative followed by amination, cyclisation and deprotection steps.