[(2R,3S,5R)-5-[5-hydroxy-3-(methoxymethyl)-2,4-dioxo-1-(phenylmethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate | 159626-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,3S,5R)-5-[5-hydroxy-3-(methoxymethyl)-2,4-dioxo-1-(phenylmethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 159626-09-2
• 化学式: C₃₇H₃₇N₃O₁₀
• 分子量: 683.715
• InChiKey: XTZUQVHSUUCCAS-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-[5-hydroxy-3-(methoxymethyl)-2,4-dioxo-1-(phenylmethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate 在 tris-(dibenzylideneacetone)dipalladium(0) 2,3,5-三甲基吡啶 、 三(2-呋喃基)膦 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-<(Benzyloxy)methyl>-5-<4-(benzyloxy)phenyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione
  参考文献：
  名称：

  A New Efficient Route to 5-Substituted .beta.-2'-Deoxyribosylpyrrolo[2,3-d]pyrimidines. Palladium-Catalyzed Functionalizations of a C-5 Triflate Intermediate

  摘要：

  An efficient synthesis of a beta-2'-deoxyribosyl-5 -[(trifluoromethanesulfonyl)oxy]pyrrolo[2,3-d]pyrimidine- 2,4-dione 9, starting from 6-chlorouracil, is presented along with its subsequent functionalization at C-5 using four types of palladium-catalyzed reactions.

  DOI：

  10.1021/jo00102a011
• 作为产物：
  描述：

  5-Acetoxy-1-<(benzyloxy)methyl>-7-<2'-deoxy-3',5'-di-O-(p-toluoyl)-D-erythro-pentofuranosyl>-3-(methoxymethyl)pyrrolo<2,3-d>pyrimidine-2,4-dione 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成 [(2R,3S,5R)-5-[5-hydroxy-3-(methoxymethyl)-2,4-dioxo-1-(phenylmethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate 、 [(2R,3S,5S)-5-[5-hydroxy-3-(methoxymethyl)-2,4-dioxo-1-(phenylmethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
  参考文献：
  名称：

  A New Efficient Route to 5-Substituted .beta.-2'-Deoxyribosylpyrrolo[2,3-d]pyrimidines. Palladium-Catalyzed Functionalizations of a C-5 Triflate Intermediate

  摘要：

  An efficient synthesis of a beta-2'-deoxyribosyl-5 -[(trifluoromethanesulfonyl)oxy]pyrrolo[2,3-d]pyrimidine- 2,4-dione 9, starting from 6-chlorouracil, is presented along with its subsequent functionalization at C-5 using four types of palladium-catalyzed reactions.

  DOI：

  10.1021/jo00102a011

文献信息

• A New Efficient Route to 5-Substituted .beta.-2'-Deoxyribosylpyrrolo[2,3-d]pyrimidines. Palladium-Catalyzed Functionalizations of a C-5 Triflate Intermediate
  作者：Eric D. Edstrom、Yuan Wei

  DOI：10.1021/jo00102a011

  日期：1994.11

  An efficient synthesis of a beta-2'-deoxyribosyl-5 -[(trifluoromethanesulfonyl)oxy]pyrrolo[2,3-d]pyrimidine- 2,4-dione 9, starting from 6-chlorouracil, is presented along with its subsequent functionalization at C-5 using four types of palladium-catalyzed reactions.