8-[[(3aR,6R,6aR)-4-(5-tert-butyl-2-methylphenyl)sulfanyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-7-benzyl-6-methoxypurine | 1393082-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-[[(3aR,6R,6aR)-4-(5-tert-butyl-2-methylphenyl)sulfanyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-7-benzyl-6-methoxypurine
• CAS: 1393082-78-4
• 化学式: C₃₂H₃₈N₄O₅S
• 分子量: 590.744
• InChiKey: RJWMPNHVKGIQNU-BUKJMKFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  8-[[(3aR,6R,6aR)-4-(5-tert-butyl-2-methylphenyl)sulfanyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-7-benzyl-6-methoxypurine 在 dimethyl(methylthio)sulfonium tetrafluoroborate 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以74%的产率得到9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-7-benzyl-6-methoxypurin-8-one
  参考文献：
  名称：

  Intramolecular glycosylation as a regio- and stereocontrolled approach for the synthesis of 8-oxo-purine nucleosides

  摘要：

  Intramolecular glycosylation of purine derivatives that are temporarily connected to the 5 position of ribofuranosyl donors at their 8 position through an ethereal linkage leads to 8-oxo-purine beta-nucleosides in a stereoselective manner. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.055
• 作为产物：
  描述：

  6-methoxy-7-benzylpurine 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 8-[[(3aR,6R,6aR)-4-(5-tert-butyl-2-methylphenyl)sulfanyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-7-benzyl-6-methoxypurine
  参考文献：
  名称：

  Intramolecular glycosylation as a regio- and stereocontrolled approach for the synthesis of 8-oxo-purine nucleosides

  摘要：

  Intramolecular glycosylation of purine derivatives that are temporarily connected to the 5 position of ribofuranosyl donors at their 8 position through an ethereal linkage leads to 8-oxo-purine beta-nucleosides in a stereoselective manner. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.055

文献信息

• Intramolecular glycosylation as a regio- and stereocontrolled approach for the synthesis of 8-oxo-purine nucleosides
  作者：Hideyuki Sugimura、Daisuke Nitta

  DOI：10.1016/j.tetlet.2012.06.055

  日期：2012.8

  Intramolecular glycosylation of purine derivatives that are temporarily connected to the 5 position of ribofuranosyl donors at their 8 position through an ethereal linkage leads to 8-oxo-purine beta-nucleosides in a stereoselective manner. (c) 2012 Elsevier Ltd. All rights reserved.