9-<3-Azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-arabinofuranosyl>adenine | 132980-95-1

• 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-<3-Azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-arabinofuranosyl>adenine
• 英文别名: 9-[3-Azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-arabinofuranosyl]adenine
• CAS: 132980-95-1
• 化学式: C₁₆H₂₆N₈O₃Si
• 分子量: 406.52
• InChiKey: PHAKXFOHXJJHSS-DSKWVYQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  157.07
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  9-<3-Azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-arabinofuranosyl>adenine 在 4-二甲氨基吡啶 、 叠氮化锂 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 生成 9-<5-O-(tert-Butyldimethylsilyl)-2,3-diazido-2,3-dideoxy-β-D-ribofuranosyl>adenine
  参考文献：
  名称：

  Nucleic acid related compounds. 64. Synthesis of 2',3'-diazido-2',3'-dideoxyadenosine and 2',3'-diamino-2',3'-dideoxyadenosine from 9-(.beta.-D-arabinofuranosyl)adenine

  摘要：

  Treatment of 9-(beta-D-arabinofuranosyl)adenine (1) with triphenylphosphine and diethyl azodicarboxylate gave 9-(2,3-anhydro-beta-D-lyxofuranosyl)adenine (2). Treatment of 2 with lithium azide and protection of the major product gave 9-[3-azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-beta-D-arabinofuranosyl]adenine (4). Trifluoromethanesulfonylation of 4 and treatment of the resulting triflate 5 with lithium azide gave 9-(5-O-TBDMS-2,3-diazido-2,3-dideoxy-beta-D-ribofuranosyl)adenine (6). Deprotection of 6 gave 2',3'-diazido-2',3'-dideoxyadenosine (7), which was hydrogenated to give the secondary diamino nucleoside analogue, 2',3'-diamino-2',3'-dideoxyadenosine (8). Biological rationale for the synthesis of nucleoside analogues 7 and 8 is discussed.

  DOI：

  10.1021/jo00010a042
• 作为产物：
  描述：

  阿糖腺苷 在 咪唑 、 叠氮化锂 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 生成 9-<3-Azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-arabinofuranosyl>adenine
  参考文献：
  名称：

  Nucleic acid related compounds. 64. Synthesis of 2',3'-diazido-2',3'-dideoxyadenosine and 2',3'-diamino-2',3'-dideoxyadenosine from 9-(.beta.-D-arabinofuranosyl)adenine

  摘要：

  Treatment of 9-(beta-D-arabinofuranosyl)adenine (1) with triphenylphosphine and diethyl azodicarboxylate gave 9-(2,3-anhydro-beta-D-lyxofuranosyl)adenine (2). Treatment of 2 with lithium azide and protection of the major product gave 9-[3-azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-beta-D-arabinofuranosyl]adenine (4). Trifluoromethanesulfonylation of 4 and treatment of the resulting triflate 5 with lithium azide gave 9-(5-O-TBDMS-2,3-diazido-2,3-dideoxy-beta-D-ribofuranosyl)adenine (6). Deprotection of 6 gave 2',3'-diazido-2',3'-dideoxyadenosine (7), which was hydrogenated to give the secondary diamino nucleoside analogue, 2',3'-diamino-2',3'-dideoxyadenosine (8). Biological rationale for the synthesis of nucleoside analogues 7 and 8 is discussed.

  DOI：

  10.1021/jo00010a042