9-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-6-[(RS)-1-hydroxy-2-methoxyethyl]purine | 1087161-06-5

• 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: 9-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-6-[(RS)-1-hydroxy-2-methoxyethyl]purine
• 英文别名: 1-[9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-6-yl]-2-methoxyethanol
• CAS: 1087161-06-5
• 化学式: C₃₁H₆₀N₄O₆Si₃
• 分子量: 669.097
• InChiKey: MOJNHCRJOJLSAZ-PFNIOKPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.21
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  9-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-6-[(RS)-1-hydroxy-2-methoxyethyl]purine 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以75%的产率得到6-[(RS)-1-hydroxy-2-methoxyethyl]-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
• 作为产物：
  描述：

  9-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-6-[(RS)-oxiran-2-yl]purine 、 sodium methylate 在 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以37%的产率得到9-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-6-[(RS)-1-hydroxy-2-methoxyethyl]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.