1,2-O-Isopropylidene-5-deoxy-5-phthalimido-D-xylofuranose | 145661-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,2-O-Isopropylidene-5-deoxy-5-phthalimido-D-xylofuranose
• 英文别名: 2-[[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl]isoindole-1,3-dione
• CAS: 145661-19-4
• 化学式: C₁₆H₁₇NO₆
• 分子量: 319.314
• InChiKey: KOHGPJVJHMLGBN-NWJSVONSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-Isopropylidene-5-deoxy-5-phthalimido-D-xylofuranose 在 sodium tetrahydroborate 、 叠氮基三甲基硅烷 、 三氟化硼乙醚 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  D-xylofuranose: Conversion to its' 3,5-oxetane via an unusual reductive displacement of phthalimide and subsequent regioselective ring opening.

  摘要：

  3,5-anhydro-1,2-O-isopropylidene-alpha-D-xylofuranose has been prepared from the corresponding 5-phthalimido derivative in quantitative yield, and its' formation involves an unusual phthalimide substitution in the presence of sodium borohydride in methanol. A mechanism is proposed for this unusual cyclisation, which involves initial activation of the phthalimide. Subsequent Lewis-acid catalysed ring openings have been achieved in a regiospecific manner.

  DOI：

  10.1016/s0040-4020(01)88323-x
• 作为产物：
  描述：

  1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 在 potassium phtalimide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以66%的产率得到1,2-O-Isopropylidene-5-deoxy-5-phthalimido-D-xylofuranose
  参考文献：
  名称：

  D-xylofuranose: Conversion to its' 3,5-oxetane via an unusual reductive displacement of phthalimide and subsequent regioselective ring opening.

  摘要：

  3,5-anhydro-1,2-O-isopropylidene-alpha-D-xylofuranose has been prepared from the corresponding 5-phthalimido derivative in quantitative yield, and its' formation involves an unusual phthalimide substitution in the presence of sodium borohydride in methanol. A mechanism is proposed for this unusual cyclisation, which involves initial activation of the phthalimide. Subsequent Lewis-acid catalysed ring openings have been achieved in a regiospecific manner.

  DOI：

  10.1016/s0040-4020(01)88323-x

文献信息

• D-xylofuranose: Conversion to its' 3,5-oxetane via an unusual reductive displacement of phthalimide and subsequent regioselective ring opening.
  作者：Nigel G. Cooke、D.Alan Jones、Andrew Whiting

  DOI：10.1016/s0040-4020(01)88323-x

  日期：1992.1

  3,5-anhydro-1,2-O-isopropylidene-alpha-D-xylofuranose has been prepared from the corresponding 5-phthalimido derivative in quantitative yield, and its' formation involves an unusual phthalimide substitution in the presence of sodium borohydride in methanol. A mechanism is proposed for this unusual cyclisation, which involves initial activation of the phthalimide. Subsequent Lewis-acid catalysed ring openings have been achieved in a regiospecific manner.