5-chloro-5-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine | 828249-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-5-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine
• CAS: 828249-04-3
• 化学式: C₁₆H₂₄ClNO₇
• 分子量: 377.822
• InChiKey: JETZBGHMLRKCHP-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-chloro-5-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、2.67 kPa 条件下， 反应 0.25h， 以92%的产率得到1,5-anhydro-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine
  参考文献：
  名称：

  d-Ribofuranosylenamine: a versatile starting material for preparing azasugar thioglycosides and building blocks for thioureylene-di-nucleosides

  摘要：

  Six-membered azasugar thioglycosides (piperidines) are prepared from a beta-D-ribofuranosylenamine, with a 1,5-anhydro derivative being the key intermediate. The alpha-anomer of the same D-ribofuranosylenamine is transformed into a 5-deoxy-5-isothiocyanato derivative, useful for preparing D-ribosylamino derivatives with a non-ionic thiourea bridge, isosteric of the phosphate bridge. The prepared thioureas are potential building blocks for the synthesis of thioureylene-di-nucleosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.012
• 作为产物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine 在 吡啶 、 甲基磺酰氯 作用下， 反应 72.0h， 以70%的产率得到5-chloro-5-deoxy-N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine
  参考文献：
  名称：

  d-Ribofuranosylenamine: a versatile starting material for preparing azasugar thioglycosides and building blocks for thioureylene-di-nucleosides

  摘要：

  Six-membered azasugar thioglycosides (piperidines) are prepared from a beta-D-ribofuranosylenamine, with a 1,5-anhydro derivative being the key intermediate. The alpha-anomer of the same D-ribofuranosylenamine is transformed into a 5-deoxy-5-isothiocyanato derivative, useful for preparing D-ribosylamino derivatives with a non-ionic thiourea bridge, isosteric of the phosphate bridge. The prepared thioureas are potential building blocks for the synthesis of thioureylene-di-nucleosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.012