t-butyl [(3R,4S)-4-(hydroxymethyl)-1-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetyl]pyrrolidin-3-yl]carbamate | 1050504-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 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)-3-t-butoxycarbonylamino-4-hydroxymethyl-1-thymidyacetylpyrrolidine；3-t-butoxycarbonylamino-4-hydroxymethyl-1-thymidyacetylpyrrolidine；tert-butyl N-[(3R,4S)-4-(hydroxymethyl)-1-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]pyrrolidin-3-yl]carbamate
• CAS: 1050504-37-4
• 化学式: C₁₇H₂₆N₄O₆
• 分子量: 382.417
• InChiKey: OQGWVVOLQBUIJQ-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  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 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成 ((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：

  在 甲醇 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 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 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.17h， 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

文献信息

• WO2008/101515
  申请人：——

  公开号：——

  公开（公告）日：——