t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl]pyrrolidin-3-yl]carbamate | 1613255-81-4

• 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: t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl]pyrrolidin-3-yl]carbamate
• 英文别名: [(3s,4r)-4-(t-Butoxycarbonylamino)-1-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)acetyl]pyrrolidin-3-yl]methyl carbonochloridate；[(3S,4R)-1-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-3-yl]methyl carbonochloridate
• CAS: 1613255-81-4
• 化学式: C₁₈H₂₅ClN₄O₇
• 分子量: 444.872
• InChiKey: WRZOPVYPMQEIOF-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-[(benzoyloxy)methyl]-1-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl]pyrrolidin-3-aminium 2,2,2-trifluoroacetate 、 t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl]pyrrolidin-3-yl]carbamate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以149 mg的产率得到((3S,4R)-4-(((((3S,4R)-4-((tert-butoxycarbonyl)amino)-1-(2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl)pyrrolidin-3-yl)methoxy)carbonyl)amino)-1-(2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl)pyrrolidin-3-yl)methyl benzoate
  参考文献：
  名称：

  Analogues of nucleosides: synthesis of chiral pyrrolidin-2-ones or pyrrolidines-bearing nucleobases

  摘要：

  Novel analogues of nucleosides tethered on a chiral pyrrolidin-2-one were prepared, but the imide functionality was unstable under basic conditions. Thus, the carbonyl group was removed from pyrrolidin-2-one, and nucleoside analogues bearing a pyrrolidine ring were synthesized, which were unaffected under basic conditions. A nucleoside dimer was also obtained, bearing a carbamate linkage between two units.Graphics for use in the Table of Contents.

  DOI：

  10.1007/s00706-014-1251-4
• 作为产物：
  描述：

  [(3S,4R)-4-(t-butoxycarbonylamino)pyrrolidin-3-yl]methyl benzoate 在 甲醇 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.0h， 生成 t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl]pyrrolidin-3-yl]carbamate
  参考文献：
  名称：

  Analogues of nucleosides: synthesis of chiral pyrrolidin-2-ones or pyrrolidines-bearing nucleobases

  摘要：

  Novel analogues of nucleosides tethered on a chiral pyrrolidin-2-one were prepared, but the imide functionality was unstable under basic conditions. Thus, the carbonyl group was removed from pyrrolidin-2-one, and nucleoside analogues bearing a pyrrolidine ring were synthesized, which were unaffected under basic conditions. A nucleoside dimer was also obtained, bearing a carbamate linkage between two units.Graphics for use in the Table of Contents.

  DOI：

  10.1007/s00706-014-1251-4