N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-β-D-ribofuranosylamine | 828249-03-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-β-D-ribofuranosylamine
• CAS: 828249-03-2
• 化学式: C₁₇H₂₇NO₁₀S
• 分子量: 437.468
• InChiKey: MMXJRBOYMVRITJ-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  135.69
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-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91%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：

  甲基磺酰氯 、 N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-β-D-ribofuranosylamine 在 吡啶 作用下， 反应 15.0h， 以70%的产率得到N-(2,2-diethoxycarbonylvinyl)-2,3-O-isopropylidene-5-O-mesyl-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