9-deaza-2'-deoxyxanthosine | 1446175-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-deaza-2'-deoxyxanthosine
• 英文别名: 7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,5-dihydropyrrolo[3,2-d]pyrimidine-2,4-dione
• CAS: 1446175-03-6
• 化学式: C₁₁H₁₃N₃O₅
• 分子量: 267.241
• InChiKey: BFGXMYJNISKENL-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-bis-benzyloxy-5H-7-(β-D-glycero-pentofuran-3′-ulos-1′-yl)pyrrolo[3,2-d]pyrimidine 在 palladium 10% on activated carbon 、 甲酸铵 、 三乙酰氧基硼氢化钠 作用下， 以 甲醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 8.0h， 生成 9-deaza-2'-deoxyxanthosine
  参考文献：
  名称：

  Synthesis of 2′-Deoxy-9-deaza Nucleosides Using Heck Methodology

  摘要：

  During the synthesis of a series of 2'-deoxy-9-deaza nucleosides using Heck methodology, the necessity for a pyrrole protecting group was discovered. The results of this brief study revealed that the benzyloxymethyl (BOM) group proved optimal, and Heck coupling using Jeffery conditions increased the coupling yield significantly. The results are reported herein.

  DOI：

  10.1021/jo400913k

文献信息

• Synthesis of 2′-Deoxy-9-deaza Nucleosides Using Heck Methodology
  作者：Kartik Temburnikar、Kelin Brace、Katherine L. Seley-Radtke

  DOI：10.1021/jo400913k

  日期：2013.7.19

  During the synthesis of a series of 2'-deoxy-9-deaza nucleosides using Heck methodology, the necessity for a pyrrole protecting group was discovered. The results of this brief study revealed that the benzyloxymethyl (BOM) group proved optimal, and Heck coupling using Jeffery conditions increased the coupling yield significantly. The results are reported herein.