(3S,4S)-4-(adenin-9-yl)-1-N-tert-butyloxycarbonyl-3-(4,4'-dimethoxytrityloxy)pyrrolidine | 926913-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3S,4S)-4-(adenin-9-yl)-1-N-tert-butyloxycarbonyl-3-(4,4'-dimethoxytrityloxy)pyrrolidine
• CAS: 926913-27-1
• 化学式: C₃₅H₃₈N₆O₅
• 分子量: 622.724
• InChiKey: NDOJZMYPMFBQLU-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  126.85
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-(adenin-9-yl)-1-N-tert-butyloxycarbonyl-3-(4,4'-dimethoxytrityloxy)pyrrolidine 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以78%的产率得到(3S,4S)-4-(adenin-9-yl)-3-hydroxypyrrolidine
  参考文献：
  名称：

  Synthesis of diastereomeric 3-hydroxy-4-pyrrolidinyl derivatives of nucleobases

  摘要：

  The work deals with the synthesis of hydroxypyrrolidine analogs of nucleosides. Starting from the optically pure L- or D-tartaric acid, we improved the synthesis of enantiomeric trans-3,4-dihydroxypyrrolidines and elaborated a procedure for the synthesis of all possible diastereoisomers of 3-hydroxy-4-pyrrolidinyl derivatives of both purine and pyrimidine nucleobases. The prepared compounds were tested for cytostatic and antiviral properties but no significant activity was found. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.047
• 作为产物：
  描述：

  (3S,4R)-1-N-tert-butyloxycarbonyl-3-(4,4'-dimethoxytrityloxy)-4-hydroxypyrrolidine 在 4-二甲氨基吡啶 、 caesium carbonate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 97.0h， 生成 (3S,4S)-4-(adenin-9-yl)-1-N-tert-butyloxycarbonyl-3-(4,4'-dimethoxytrityloxy)pyrrolidine
  参考文献：
  名称：

  Synthesis of diastereomeric 3-hydroxy-4-pyrrolidinyl derivatives of nucleobases

  摘要：

  The work deals with the synthesis of hydroxypyrrolidine analogs of nucleosides. Starting from the optically pure L- or D-tartaric acid, we improved the synthesis of enantiomeric trans-3,4-dihydroxypyrrolidines and elaborated a procedure for the synthesis of all possible diastereoisomers of 3-hydroxy-4-pyrrolidinyl derivatives of both purine and pyrimidine nucleobases. The prepared compounds were tested for cytostatic and antiviral properties but no significant activity was found. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.047