2,4-bis-benzyloxy-5-N-benzyloxymethy-7-(β-D-glycero-pentofuran-3′-ulos-1′-yl)pyrrolo[3,2-d]pyrimidine | 1446175-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 2,4-bis-benzyloxy-5-N-benzyloxymethy-7-(β-D-glycero-pentofuran-3′-ulos-1′-yl)pyrrolo[3,2-d]pyrimidine
• 英文别名: (2R,5R)-5-[2,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolo[3,2-d]pyrimidin-7-yl]-2-(hydroxymethyl)oxolan-3-one
• CAS: 1446175-10-5
• 化学式: C₃₃H₃₁N₃O₆
• 分子量: 565.626
• InChiKey: VBWOTHVKBGXPSZ-FQLXRVMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4-bis-benzyloxy-5-N-benzyloxymethy-7-(β-D-glycero-pentofuran-3′-ulos-1′-yl)pyrrolo[3,2-d]pyrimidine 在 三乙酰氧基硼氢化钠 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 以60%的产率得到1′-β-[7-(2,4-bis-benzyloxy-5-benzyloxymethypyrrolo[3,2-d]pyrimidine)]-2′-deoxyribofuranose
  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
• 作为产物：
  描述：

  4,5-哒嗪二醇,六氢-3-(羟甲基)-,(3R,4R,5R)- 在 N-碘代丁二酰亚胺 、 四丁基氯化铵 、 palladium diacetate 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 50.0h， 生成 2,4-bis-benzyloxy-5-N-benzyloxymethy-7-(β-D-glycero-pentofuran-3′-ulos-1′-yl)pyrrolo[3,2-d]pyrimidine
  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.