9-(2,3-Diazido-2,3-dideoxy-β-D-ribofuranosyl)adenine | 119644-21-2

• 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-(2,3-Diazido-2,3-dideoxy-β-D-ribofuranosyl)adenine
• 英文别名: 2',3'-diazido-2',3'-dideoxyadenosine；[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-diazidooxolan-2-yl]methanol
• CAS: 119644-21-2
• 化学式: C₁₀H₁₁N₁₁O₂
• 分子量: 317.27
• InChiKey: WQZLKYFRGKFHEZ-PLDPKQSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  9-(2,3-Diazido-2,3-dideoxy-β-D-ribofuranosyl)adenine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 N,N-二甲基乙酰胺 、 苯 为溶剂， 反应 0.5h， 以90%的产率得到2',3'-diamino-2',3'-dideoxyadenosine
  参考文献：
  名称：

  用三丁基锡烷将叠氮化物有效还原为胺。氨基和二氨基脱氧核苷的高产率合成

  摘要：

  用三丁基锡烷/ AIBN在热苯/ DMAC中（或苯中甲硅烷基保护的衍生物）处理未保护的叠氮基-脱氧核苷，导致形成相应的氨基-脱氧核苷，分离产率高。指示了根本过程。

  DOI：

  10.1016/0040-4039(91)80150-5
• 作为产物：
  描述：

  阿糖腺苷 在 咪唑 、 4-二甲氨基吡啶 、 叠氮化锂 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.09h， 生成 9-(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

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：——
• 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
  作者：Y. C. Jack Chen、Fritz Hansske、Kim D. Janda、Morris J. Robins

  DOI：10.1021/jo00010a042

  日期：1991.5

  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.
• Efficient reduction of azides to amines with tributylstannane. high-yield syntheses of amino and diamino deoxynucleosides
  作者：Mirna C. Samano、Morris J. Robins

  DOI：10.1016/0040-4039(91)80150-5

  日期：1991.10

  azido-deoxynucleosides with tributylstannane/AIBN in hot benzene/DMAC (or silyl-protected derivatives in benzene) resulted in formation of the corresponding amino-deoxynucleosides in high isolated yields. A radical process is indicated.

  用三丁基锡烷/ AIBN在热苯/ DMAC中（或苯中甲硅烷基保护的衍生物）处理未保护的叠氮基-脱氧核苷，导致形成相应的氨基-脱氧核苷，分离产率高。指示了根本过程。