N-[1-[(2R,3R,5S)-5-(hydroxymethyl)-3-methyloxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide | 1027366-46-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N-[1-[(2R,3R,5S)-5-(hydroxymethyl)-3-methyloxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 1027366-46-6
• 化学式: C₁₇H₁₉N₃O₄
• 分子量: 329.356
• InChiKey: VUYZUDMHAQFPQP-PVXIVEMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[1-[(2R,3R,5S)-5-(hydroxymethyl)-3-methyloxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide 在 氨 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以84%的产率得到1-(2,3-dideoxy-2-C-methyl-β-D-erythro-pentofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis of 2′-C-α-Methyl-2′,3′-dideoxynucleosides

  摘要：

  A general method for the synthesis of 2'-C-alpha-methyl-2',3'-dideoxynucleosides is presented. Stereofacial selectivity of the 2-C-methylation reaction of gamma-lactone has been investigated, in which the presence of a bulky group at the 5-hydroxymethyl produced the alpha-isomer as a major product. During glycosylation, the alpha-methyl group directed the formation of nucleosides in favor of the beta-isomer. This methodology is applied to the synthesis of some new pyrimidine and purine nucleosides.

  DOI：

  10.1080/07328319608002379
• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 9.58h， 生成 N-[1-[(2R,3R,5S)-5-(hydroxymethyl)-3-methyloxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
  参考文献：
  名称：

  Synthesis of 2′-C-α-Methyl-2′,3′-dideoxynucleosides

  摘要：

  A general method for the synthesis of 2'-C-alpha-methyl-2',3'-dideoxynucleosides is presented. Stereofacial selectivity of the 2-C-methylation reaction of gamma-lactone has been investigated, in which the presence of a bulky group at the 5-hydroxymethyl produced the alpha-isomer as a major product. During glycosylation, the alpha-methyl group directed the formation of nucleosides in favor of the beta-isomer. This methodology is applied to the synthesis of some new pyrimidine and purine nucleosides.

  DOI：

  10.1080/07328319608002379

文献信息

• Synthesis of 2′-C-α-Methyl-2′,3′-dideoxynucleosides
  作者：Indrajit Giri、Pascal J. Bolon、Chung K. Chu

  DOI：10.1080/07328319608002379

  日期：1996.1

  A general method for the synthesis of 2'-C-alpha-methyl-2',3'-dideoxynucleosides is presented. Stereofacial selectivity of the 2-C-methylation reaction of gamma-lactone has been investigated, in which the presence of a bulky group at the 5-hydroxymethyl produced the alpha-isomer as a major product. During glycosylation, the alpha-methyl group directed the formation of nucleosides in favor of the beta-isomer. This methodology is applied to the synthesis of some new pyrimidine and purine nucleosides.