(1R,3S)-1-(3-pivaloyloxymethyl-1,3-dihydrobenzo[c]furan-1-yl)uracil | 459831-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (1R,3S)-1-(3-pivaloyloxymethyl-1,3-dihydrobenzo[c]furan-1-yl)uracil
• 英文别名: [(1S,3R)-3-(2,4-dioxopyrimidin-1-yl)-1,3-dihydro-2-benzofuran-1-yl]methyl 2,2-dimethylpropanoate
• CAS: 459831-03-9
• 化学式: C₁₈H₂₀N₂O₅
• 分子量: 344.367
• InChiKey: PSIUEADBKWLLHE-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3S)-1-(3-pivaloyloxymethyl-1,3-dihydrobenzo[c]furan-1-yl)uracil 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以93%的产率得到(1R,3S)-1-(3-Hydroxymethyl-1,3-dihydroxybenzo[c]furan-1-yl)uracil
  参考文献：
  名称：

  Enantiomeric d4T analogues and their structural determination

  摘要：

  Asymmetric synthesis of d4T analogues having a benzo[c]furan moiety with two asymmetric carbon atoms was realized using Sharpless asymmetric dihydroxylation as the key step in a synthesis starting from o-phthalaldehyde. Enantiomeric purities were determined by analytical chiral HPLC with an amylose-derived stationary phase, while the absolute configurations were established by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00106-4
• 作为产物：
  描述：

  邻苯二甲醛 在 盐酸 、 甲醇 、 AD-mix-α 、 正丁基锂 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (1R,3S)-1-(3-pivaloyloxymethyl-1,3-dihydrobenzo[c]furan-1-yl)uracil
  参考文献：
  名称：

  Enantiomeric d4T analogues and their structural determination

  摘要：

  Asymmetric synthesis of d4T analogues having a benzo[c]furan moiety with two asymmetric carbon atoms was realized using Sharpless asymmetric dihydroxylation as the key step in a synthesis starting from o-phthalaldehyde. Enantiomeric purities were determined by analytical chiral HPLC with an amylose-derived stationary phase, while the absolute configurations were established by X-ray crystallography. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00106-4