(1S)-1,2,3,4,5-penta-O-acetyl-D-arabinose 1-(dimethylphosphonate) | 53910-63-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S)-1,2,3,4,5-penta-O-acetyl-D-arabinose 1-(dimethylphosphonate)
• 英文别名: (1S)-1,2,3,4,5-Penta-O-acetyl-D-arabit-1-phosphonsaeure-dimethylester；[(2R,3R,4S,5S)-2,3,4,5-tetraacetyloxy-5-[dimethoxy(oxido)phosphaniumyl]pentyl] acetate
• CAS: 53910-63-7
• 化学式: C₁₇H₂₇O₁₃P
• 分子量: 470.367
• InChiKey: LTCHWCJJSFSPJS-NCOADZHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  173
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  ((1S)-1-hydroxy-D-arabinitol-1-yl)-phosphonic acid dimethyl ester 、 乙酸酐 在 吡啶 作用下， 反应 36.0h， 以60%的产率得到(1S)-1,2,3,4,5-penta-O-acetyl-D-arabinose 1-(dimethylphosphonate)
  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