6-[(RS)-1,2-dihydroxyethyl]-9-(β-D-ribofuranosyl)purine | 1087161-23-6

• 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: 6-[(RS)-1,2-dihydroxyethyl]-9-(β-D-ribofuranosyl)purine
• 英文别名: (2R,3R,4S,5R)-2-[6-(1,2-dihydroxyethyl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1087161-23-6
• 化学式: C₁₂H₁₆N₄O₆
• 分子量: 312.282
• InChiKey: HLJQNWACZBMGFZ-NZUOTHCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  9-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-6-[(RS)-1,2-dihydroxyethyl]purine 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以93%的产率得到6-[(RS)-1,2-dihydroxyethyl]-9-(β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Synthesis of diverse 6-(1,2-disubstituted ethyl)purine bases and nucleosides via 6-(oxiran-2-yl)purines

  摘要：

  Dihydroxylation of 6-vinylpurines with t-BuOOH and OSO4 gave 6-(1,2-dihydroxyethyl)purines 2, while the epoxidation with H2WO4 and t-BuOOH afforded 6-(oxiran-2-yl)purines 3. Oxirane ring-opening reactions of 3 with diverse nucleophiles gave a series of title 6-(1,2-disubstituted ethyl)purine bases and nucleosides, which were tested for cytostatic and antiviral activities. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.08.074

文献信息

• Synthesis of diverse 6-(1,2-disubstituted ethyl)purine bases and nucleosides via 6-(oxiran-2-yl)purines
  作者：Martin Kuchař、Radek Pohl、Blanka Klepetářová、Michal Hocek

  DOI：10.1016/j.tet.2008.08.074

  日期：2008.11

  Dihydroxylation of 6-vinylpurines with t-BuOOH and OSO4 gave 6-(1,2-dihydroxyethyl)purines 2, while the epoxidation with H2WO4 and t-BuOOH afforded 6-(oxiran-2-yl)purines 3. Oxirane ring-opening reactions of 3 with diverse nucleophiles gave a series of title 6-(1,2-disubstituted ethyl)purine bases and nucleosides, which were tested for cytostatic and antiviral activities. (C) 2008 Published by Elsevier Ltd.