(1R,2S,6S,8R)-2-[(6-hydroxy-9H-purin-9-yl)methyl]-9,9-dimethyl-4-ethoxy-3,5-dioxatricyclo[6.1.1.0(2,6)]decane | 1239953-48-0

• 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: (1R,2S,6S,8R)-2-[(6-hydroxy-9H-purin-9-yl)methyl]-9,9-dimethyl-4-ethoxy-3,5-dioxatricyclo[6.1.1.0(2,6)]decane
• 英文别名: 9-[[(1R,2S,6S,8R)-4-ethoxy-9,9-dimethyl-3,5-dioxatricyclo[6.1.1.02,6]decan-2-yl]methyl]-1H-purin-6-one
• CAS: 1239953-48-0
• 化学式: C₁₈H₂₄N₄O₄
• 分子量: 360.413
• InChiKey: VJXKSJLLTDITJD-DENWEWIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,6S,8R)-2-[(6-hydroxy-9H-purin-9-yl)methyl]-9,9-dimethyl-4-ethoxy-3,5-dioxatricyclo[6.1.1.0(2,6)]decane 在 盐酸 、 水 作用下， 反应 12.0h， 以67%的产率得到(1R,2S,3S,5R)-2-[(6-hydroxy-9H-purin-9-yl)methyl]-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol hydrochloride
  参考文献：
  名称：

  Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols

  摘要：

  Starting from (1R,25,3S.5R)- and (15,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3 1.1]heptane-2.2'-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN(3) resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of ( -)-8 and (+)-8 resulted in adenine-. cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.04.054
• 作为产物：
  描述：

  (1R,2S,6S,8R)-2-[(6-chloro-9H-purin-9-yl)methyl]-9,9-dimethyl-4-ethoxy-3,5-dioxatricyclo[6.1.1.0(2,6)]decane 在 水 、 sodium hydroxide 作用下， 反应 5.0h， 以85%的产率得到(1R,2S,6S,8R)-2-[(6-hydroxy-9H-purin-9-yl)methyl]-9,9-dimethyl-4-ethoxy-3,5-dioxatricyclo[6.1.1.0(2,6)]decane
  参考文献：
  名称：

  Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols

  摘要：

  Starting from (1R,25,3S.5R)- and (15,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3 1.1]heptane-2.2'-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN(3) resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of ( -)-8 and (+)-8 resulted in adenine-. cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.04.054

文献信息

• Carbocyclic nucleosides from enantiomeric, α-pinane-based aminodiols
  作者：Zsolt Szakonyi、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2010.04.054

  日期：2010.4

  Starting from (1R,25,3S.5R)- and (15,2R,3R,5S)-6,6-dimethylspiro[bicyclo[3 1.1]heptane-2.2'-oxiran]-3-ol (-)-8 and (+)-8, two comparative syntheses were developed for pinane-based chiral carbocyclic nucleosides The regioselective ring opening of the spiro-oxirane ring of (-)-8 and (+)-8 with NaN(3) resulted in azidodiols (-)-9 and (+)-9. Catalytic reduction of (-)-9 and (+)-9 furnished chiral aminodiols (-)-10 and (+)-10, which were transformed by linear synthesis to purine-type nucleosides 16-18 through pyrimidine intermediates. Regioselective ring opening of the oxirane ring of ( -)-8 and (+)-8 resulted in adenine-. cytosine- and uracil-based carbocyclic nucleosides 19-21 in a single-step synthesis (C) 2010 Elsevier Ltd All rights reserved