9-<3-Azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-2-O-(trifluoromethanesulfonyl)-β-D-arabinofuranosyl>adenine | 132980-96-2

• 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-2-O-(trifluoromethanesulfonyl)-β-D-arabinofuranosyl>adenine
• 英文别名: [(2R,3S,4R,5S)-2-(6-aminopurin-9-yl)-4-azido-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl] trifluoromethanesulfonate
• CAS: 132980-96-2
• 化学式: C₁₇H₂₅F₃N₈O₅SSi
• 分子量: 538.583
• InChiKey: YGNQIBMBJJJPSO-DSKWVYQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  180.21
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  9-<3-Azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-2-O-(trifluoromethanesulfonyl)-β-D-arabinofuranosyl>adenine 在 palladium on activated charcoal 叠氮化锂 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 盐酸 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.75h， 生成 2',3'-diamino-2',3'-dideoxyadenosine
  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 、 4-二甲氨基吡啶 、 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 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.34h， 生成 9-<3-Azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-2-O-(trifluoromethanesulfonyl)-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

文献信息

• CHEN, Y. -C. JACK;HANSSKE, FRITZ;JANDA, KIM D.;ROBINS, MORRIS J., J. ORG. CHEM., 56,(1991) N0, C. 3410-3413
  作者：CHEN, Y. -C. JACK、HANSSKE, FRITZ、JANDA, KIM D.、ROBINS, MORRIS J.

  DOI：——

  日期：——