(2R,3R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol | 215372-42-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2R,3R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol
• CAS: 215372-42-2
• 化学式: C₂₃H₄₀N₄O₅Si₂
• 分子量: 508.765
• InChiKey: VDIIOEXPZKLEPV-KTDPBYDISA-N

物化性质

• 沸点：
  551.2±60.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  100.75
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 在 4-二甲氨基吡啶 、 氟化铵 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 20.0h， 生成 6-甲基嘌呤2'-脱氧核糖甙
  参考文献：
  名称：

  A Novel Approach to Synthesis of 2′-Deoxy-β-D-Ribonucleosedes Via Transglycosylation of 6-Oxopurine Ribonucleosides

  摘要：

  A novel method of synthesis of 2'-deoxy-beta-D-ribonucleosides via transglycosylation of 6-oxopurine ribonucleosides is exemplified for conversion of inosine into 6-metylpurine 2'-deoxyriboside (5). The method offers high regio- and stereoselectivity as well as a good overall yield, and in these respects is superior to the fusion or anionic glycosylation procedures.

  DOI：

  10.1080/07328319808004685
• 作为产物：
  描述：

  Acetic acid (2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 在 甲醇 、 氨 作用下， 反应 3.5h， 以100%的产率得到(2R,3R,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-(6-methyl-purin-9-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol
  参考文献：
  名称：

  A Novel Approach to Synthesis of 2′-Deoxy-β-D-Ribonucleosedes Via Transglycosylation of 6-Oxopurine Ribonucleosides

  摘要：

  A novel method of synthesis of 2'-deoxy-beta-D-ribonucleosides via transglycosylation of 6-oxopurine ribonucleosides is exemplified for conversion of inosine into 6-metylpurine 2'-deoxyriboside (5). The method offers high regio- and stereoselectivity as well as a good overall yield, and in these respects is superior to the fusion or anionic glycosylation procedures.

  DOI：

  10.1080/07328319808004685

文献信息

• Convenient Syntheses of 6-Methylpurine and Related Nucleosides
  作者：Abdalla E. A. Hassan、Reham A. I. Abou-elkair、John A. Montgomery、John A. Secrist

  DOI：10.1080/15257770008035035

  日期：2000.7

  Efficient methods for the synthesis of 6-methylpurine (3), 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-6-methylpurine (8), and 6-methyl-9-beta-D-ribofuranosylpurine (5) are described. Methodology involving the (Ph3P)4Pd catalyzed cross-coupling reaction of CH3ZnBr with several different 6-chloropurine derivatives is described in high yield. This methodology now provides a facile and high-yielding synthesis

  合成6-甲基嘌呤（3），9-（2-脱氧-β-D-赤五戊呋喃糖基）-6-甲基嘌呤（8）和6-甲基-9-β-D-核呋喃呋喃糖基嘌呤的有效方法（5 ）进行了说明。以高收率描述了涉及CH3ZnBr与几种不同的6-氯嘌呤衍生物的（Ph3P）4Pd催化交叉偶联反应的方法。现在，该方法学提供了8的简便且高产率的合成方法，对于癌症基因治疗的研究而言，这是大量所需的。