5'-azido-N⁶-benzoyl-2',5'-dideoxy-adenosine | 74625-78-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 5'-azido-N⁶-benzoyl-2',5'-dideoxy-adenosine
• 英文别名: 5'-Azido-N6-benzoyl-2',5'-dideoxyadenosine；5'-Azido-N⁶-benzoyl-2',5'-dideoxyadenosine；N-[9-[(2R,4S,5R)-5-(azidomethyl)-4-hydroxyoxolan-2-yl]purin-6-yl]benzamide
• CAS: 74625-78-8
• 化学式: C₁₇H₁₆N₈O₃
• 分子量: 380.366
• InChiKey: WTCZVOYPAJWWHU-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-azido-N⁶-benzoyl-2',5'-dideoxy-adenosine 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 Succinic acid mono-[(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-({[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-methyl)-tetrahydro-furan-3-yl] ester
  参考文献：
  名称：

  Solid-Phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences

  摘要：

  Positively charged DNG oligonucleotide mixed sequences containing A/T bases were prepared by solid-phase synthesis. Synthesis proceeds in 3'-->5' direction and involves coupling of 3'-Fmoc protected thiourea in the presence of HgCl2/TEA with the corresponding 5'-amine of the growing oligo chain. DNG binding characteristics with complementary DNA and with itself have been evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00119-7
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 三甲基氯硅烷 、 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 5'-azido-N⁶-benzoyl-2',5'-dideoxy-adenosine
  参考文献：
  名称：

  Solid-Phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences

  摘要：

  Positively charged DNG oligonucleotide mixed sequences containing A/T bases were prepared by solid-phase synthesis. Synthesis proceeds in 3'-->5' direction and involves coupling of 3'-Fmoc protected thiourea in the presence of HgCl2/TEA with the corresponding 5'-amine of the growing oligo chain. DNG binding characteristics with complementary DNA and with itself have been evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00119-7

文献信息

• Synthesis of dinucleotides containing a bridged non-chiral internucleotide 5′- or 3′-phosphoramidate linkage
  作者：Matthias Mag、Joachim W. Engels

  DOI：10.1016/s0040-4020(01)81755-5

  日期：1994.8

  The synthesis of several dinucleoside phosphate derivatives which are linked by phosphoramidate bonds [3′-O-P(O)(O−)-NH-5′ or 3′-NH-P(O)(O−)-O-5′] has been accomplished. The internucleoside phosphoramidate linkage was performed using the Staudinger reaction which is directly followed by a Michaelis-Arbuzov type transformation. Due to the exclusive use of base labile blocking groups deprotection could

  通过氨基磷酸酯键[ 3'- O - P（= O）（O -）- NH -5'或3'- NH - P（= O）（O -）- O连接的几种二核苷磷酸酯衍生物的合成-5′]已经完成。使用Staudinger反应进行核苷间氨基磷酸酯键合，然后直接进行Michaelis-Arbuzov型转化。由于仅使用碱不稳定的封闭基团，因此可以非常简单地通过在55°C下用浓氨水处理24小时来轻松进行脱保护。
• A “Traceless” Staudinger Ligation for the Chemoselective Synthesis of Amide Bonds
  作者：Eliana Saxon、Joshua I. Armstrong、Carolyn R. Bertozzi

  DOI：10.1021/ol006054v

  日期：2000.7.1

  [reaction: see text] Here we report a novel modification of our previously reported "Staudinger ligation" that generates an amide bond from an azide and a specifically functionalized phosphine. This method for the selective formation of an amide bond, which does not require the orthogonal protection of distal functional groups, should find general utility in synthetic and biological chemistry.

  [反应：见正文]在这里，我们报告了对我们先前报道的“斯托丁格连接”的一种新颖修饰，该修饰从叠氮化物和经过特殊功能化的膦生成酰胺键。不需要远端官能团的正交保护的这种选择性形成酰胺键的方法应该在合成和生物化学中找到通用的用途。
• Oligonucleotide analogs with sulfamate linkages
  申请人：The Dupont Merck Pharmaceutical Company

  公开号：US05470967A1

  公开（公告）日：1995-11-28

  Oligonucleotides possessing at least one sulfamate or sulfamide internucleotides linkages. These compounds can be used as specific hybridization probes to detect complementary nucleic acid sequences.

  具有至少一个磺酰胺或磺酸酯核苷酸间键的寡核苷酸。这些化合物可用作特异性杂交探针，用于检测互补的核酸序列。
• Synthesis of sulfamide linked dinucleotide analogues
  作者：Jason Micklefield、Kevin J. Fettes

  DOI：10.1016/s0040-4039(97)01179-9

  日期：1997.7

  Novel sulfamide [-NHSO2NH-] linked dinucleotide analogues d(TnsnT) and d(TnsnA) have been synthesised from 3'- and 5'-amino nucleosides. Treatment of these amino nucleosides with catechol sulfate results in the formation of 2-hydroxyphenyl sulfamate eaters which couple smoothly in good yields with either 5'- or 3'-amines of similar nucleosides. NMR studies showed that the 3'-sulfamide group results in a preferential C3'-endo (Northern) sugar conformation. (C) 1997 Elsevier Science Ltd.
• Oligonucleotides with a nuclease-resistant sulfur-based linkage
  作者：Edward M. Huie、Mindy R. Kirshenbaum、George L. Trainor

  DOI：10.1021/jo00043a004

  日期：1992.8

  A pair of complementary oligonucleotides with an EcoR1 recognition sequence (GAATTC) bearing a novel sulfamate linkage at the cleavage site have been prepared and shown to be capable of annealing to form a stable duplex that is resistant to EcoR1 cleavage.