(1R)-2,3:4,5-di-O-isopropylidene-D-arabinose 1-(diethylphosphonate) | 158414-22-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (1R)-2,3:4,5-di-O-isopropylidene-D-arabinose 1-(diethylphosphonate)
• 英文别名: (R)-diethoxyphosphoryl-[(4S,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 158414-22-3
• 化学式: C₁₅H₂₉O₈P
• 分子量: 368.364
• InChiKey: QUDZIHWZELYJMU-FVCCEPFGSA-N

物化性质

• 沸点：
  441.8±45.0 °C(predicted)
• 密度：
  1.182±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R)-2,3:4,5-di-O-isopropylidene-D-arabinose 1-(diethylphosphonate) 在 20-50 mesh 、 Dowex-H 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 (1R)-D-arabinose 1-(diethylphosphonate)
  参考文献：
  名称：

  Cyclic Phosphonate Analogs of Hexopyranoses

  摘要：

  Acyclic and cyclic analogs of D-glucopyranose and D-mannopyranose have been prepared in which the anomeric carbon has been replaced with a phosphorus. Base-catalyzed addition of dimethyl phosphite to di-O-isopropylidene-D-arabinose followed by recrystallization yields only the acyclic gluco-isomer, through what appears to be a selective recrystallization process. The use of diethyl phosphite under similar conditions yielded only the acyclic manno-isomer. The stereochemistry of each was ascertained through comparison of the pentaacetylated derivatives 11 and 12. For the cyclic analogs 1 and 2, synthesis consists of acid-catalyzed trimethyl phosphite addition to the carbonyl of a hydroxyl-protected open-chain D-arabinose derivative, removal of a formate ester from the 4-hydroxyl group, and base-catalyzed transesterification/cyclization. All four possible cyclic alpha-hydroxy phosphonate diastereomers were synthesized in roughly equal amounts. Complete separation of the gluco- and manno-isomers was accomplished, and Homonuclear two-dimensional J-spectroscopy was used to supplement-standard NMR analysis in order to completely characterize the isolated diastereomers 21 and 22 and assign gluco- and manno-stereochemistry, respectively.

  DOI：

  10.1021/jo00090a014
• 作为产物：
  描述：

  1,2:3,4-di-O-isopropylidene-D-mannitol 在 sodium periodate 、 sodium ethanolate 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (1R)-2,3:4,5-di-O-isopropylidene-D-arabinose 1-(diethylphosphonate)
  参考文献：
  名称：

  Cyclic Phosphonate Analogs of Hexopyranoses

  摘要：

  Acyclic and cyclic analogs of D-glucopyranose and D-mannopyranose have been prepared in which the anomeric carbon has been replaced with a phosphorus. Base-catalyzed addition of dimethyl phosphite to di-O-isopropylidene-D-arabinose followed by recrystallization yields only the acyclic gluco-isomer, through what appears to be a selective recrystallization process. The use of diethyl phosphite under similar conditions yielded only the acyclic manno-isomer. The stereochemistry of each was ascertained through comparison of the pentaacetylated derivatives 11 and 12. For the cyclic analogs 1 and 2, synthesis consists of acid-catalyzed trimethyl phosphite addition to the carbonyl of a hydroxyl-protected open-chain D-arabinose derivative, removal of a formate ester from the 4-hydroxyl group, and base-catalyzed transesterification/cyclization. All four possible cyclic alpha-hydroxy phosphonate diastereomers were synthesized in roughly equal amounts. Complete separation of the gluco- and manno-isomers was accomplished, and Homonuclear two-dimensional J-spectroscopy was used to supplement-standard NMR analysis in order to completely characterize the isolated diastereomers 21 and 22 and assign gluco- and manno-stereochemistry, respectively.

  DOI：

  10.1021/jo00090a014

文献信息

• Cyclic Phosphonate Analogs of Hexopyranoses
  作者：James W. Darrow、Dale G. Drueckhammer

  DOI：10.1021/jo00090a014

  日期：1994.6

  Acyclic and cyclic analogs of D-glucopyranose and D-mannopyranose have been prepared in which the anomeric carbon has been replaced with a phosphorus. Base-catalyzed addition of dimethyl phosphite to di-O-isopropylidene-D-arabinose followed by recrystallization yields only the acyclic gluco-isomer, through what appears to be a selective recrystallization process. The use of diethyl phosphite under similar conditions yielded only the acyclic manno-isomer. The stereochemistry of each was ascertained through comparison of the pentaacetylated derivatives 11 and 12. For the cyclic analogs 1 and 2, synthesis consists of acid-catalyzed trimethyl phosphite addition to the carbonyl of a hydroxyl-protected open-chain D-arabinose derivative, removal of a formate ester from the 4-hydroxyl group, and base-catalyzed transesterification/cyclization. All four possible cyclic alpha-hydroxy phosphonate diastereomers were synthesized in roughly equal amounts. Complete separation of the gluco- and manno-isomers was accomplished, and Homonuclear two-dimensional J-spectroscopy was used to supplement-standard NMR analysis in order to completely characterize the isolated diastereomers 21 and 22 and assign gluco- and manno-stereochemistry, respectively.