(1S,2S,3S,4R)-4-hydroxy-2,3-(isopropylidenedioxy)cyclopentan-1-yl diethyl phosphate | 594857-57-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (1S,2S,3S,4R)-4-hydroxy-2,3-(isopropylidenedioxy)cyclopentan-1-yl diethyl phosphate
• 英文别名: [(3aS,4S,6R,6aS)-6-hydroxy-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl] diethyl phosphate
• CAS: 594857-57-5
• 化学式: C₁₂H₂₃O₇P
• 分子量: 310.284
• InChiKey: BWLZPNBKGUSOTI-VPOLOUISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4R)-4-hydroxy-2,3-(isopropylidenedioxy)cyclopentan-1-yl diethyl phosphate 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以81%的产率得到(-)-(3Ar,6ar)-3a,6a-二氢-2,2-二甲基-4H-环戊并-1,3-二氧代-4-酮
  参考文献：
  名称：

  A Facile Synthesis of (−)-(4R,5R)-4,5-(Isopropylidenedioxy)-2-cyclopentenone, a Useful Precursor tod-Like Carbanucleosides

  摘要：

  A facile synthesis of (-)-(4R,5R)-4,5-(isopropylidenedioxy)2-cyclopentenone ((-)-2), as a precursor to D-like carbanucleosides, is described in 5 steps from (1S,4R)-4-acetoxycyclopent-2-en-1-ol (3). Compound 3 has also been described in the literature as amenable to the formation of (+)-2, thus making both the D-like and L-like carbanucleosides available from the same readily available 3.

  DOI：

  10.1081/scc-120018765
• 作为产物：
  描述：

  (1S,4R)-4-acetoxycyclopent-2-en-1-yl diethyl phosphate 在 四氧化锇 、 氨 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 63.0h， 生成 (1S,2S,3S,4R)-4-hydroxy-2,3-(isopropylidenedioxy)cyclopentan-1-yl diethyl phosphate
  参考文献：
  名称：

  A Facile Synthesis of (−)-(4R,5R)-4,5-(Isopropylidenedioxy)-2-cyclopentenone, a Useful Precursor tod-Like Carbanucleosides

  摘要：

  A facile synthesis of (-)-(4R,5R)-4,5-(isopropylidenedioxy)2-cyclopentenone ((-)-2), as a precursor to D-like carbanucleosides, is described in 5 steps from (1S,4R)-4-acetoxycyclopent-2-en-1-ol (3). Compound 3 has also been described in the literature as amenable to the formation of (+)-2, thus making both the D-like and L-like carbanucleosides available from the same readily available 3.

  DOI：

  10.1081/scc-120018765