N6-Benzoyl-3'-amino-2',3'-dideoxyadenosine | 1028810-13-0

• 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: N6-Benzoyl-3'-amino-2',3'-dideoxyadenosine
• 英文别名: N-[9-[(2R,4S,5S)-4-amino-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 1028810-13-0
• 化学式: C₁₇H₁₈N₆O₃
• 分子量: 354.368
• InChiKey: ZBZIWWLWLNIYPJ-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N6-Benzoyl-3'-amino-2',3'-dideoxyadenosine 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  An Enzymatic Transglycosylation of Purine Bases

  摘要：

  An enzymatic transglycosylation of purine heterocyclic bases employing readily available natural nucleosides or sugar-modified nucleosides as donors of the pentofuranose fragment and recombinant nucleoside phosphorylases as biocatalysts has been investigated. An efficient enzymatic method is suggested for the synthesis of purine nucleosides containing diverse substituents at the C6 and C2 carbon atoms. The glycosylation of N-6-benzoyladenine and N-2-acetylguanine and its O-6-derivatives is not accompanied by deacylation of bases.

  DOI：

  10.1080/15257770701506343
• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 、 3'-氨基-2',3'-双脱氧鸟苷 在 purine nucleoside phosphorylase 、 potassium phosphate buffer 作用下， 以82%的产率得到N6-Benzoyl-3'-amino-2',3'-dideoxyadenosine
  参考文献：
  名称：

  An Enzymatic Transglycosylation of Purine Bases

  摘要：

  An enzymatic transglycosylation of purine heterocyclic bases employing readily available natural nucleosides or sugar-modified nucleosides as donors of the pentofuranose fragment and recombinant nucleoside phosphorylases as biocatalysts has been investigated. An efficient enzymatic method is suggested for the synthesis of purine nucleosides containing diverse substituents at the C6 and C2 carbon atoms. The glycosylation of N-6-benzoyladenine and N-2-acetylguanine and its O-6-derivatives is not accompanied by deacylation of bases.

  DOI：

  10.1080/15257770701506343

文献信息

• SOLID PHASE SYNTHESIS OF OLIGONUCLEOTIDE N3-'P5'- PHOSPHORAMIDATES
  申请人：LYNX THERAPEUTICS, INC.

  公开号：EP0882059A1

  公开（公告）日：1998-12-09
• [EN] SOLID PHASE SYNTHESIS OF OLIGONUCLEOTIDE N3'}P5' PHOSPHORAMIDATES<br/>[FR] SYNTHESE EN PHASE SOLIDE DE PHOSPHORAMIDATES N3'}P5' OLIGONUCLEOTIDIQUES
  申请人：LYNX THERAPEUTICS, INC.

  公开号：WO1997031009A1

  公开（公告）日：1997-08-28

  (EN) The invention provides a method of synthesizing oligonucleotide N3'$m(7)P5' phosphoramidates using an amine-exchange reaction of phosphoramidites in which a deprotected 3'-amino group of a solid phase supported oligonucleotide chain is exchanged for the amino portion of a 5'-phosphoramidite of an incoming monomer which has a protected 3'-amino group. The resulting internucleotide phosphoramidite linkage is then oxidized to form a stable protected phosphoramidate linkage. The method of the invention greatly improves product yields and reduces reagent usage over currently available methods for synthesizing the above class of compound.(FR) L'invention concerne un procédé de synthèse de phosphoramidates N3'$m(7)P5' oligonucléotidiques par une réaction à échange d'amines de phosphoramidites au cours de laquelle un groupe 3'-amino déprotégé d'une chaîne oligonucléotidique supportée en phase solide est échangé contre la portion amino d'un 5'-phosphoramidite d'un monomère entrant qui possède un groupe 3'-amino protégé. La liaison phosphoramidite internucléotidique résultante est ensuite oxydée pour former une liaison phosphoramidate stable et protégée. Le procédé de l'invention permet d'améliorer considérablement les rendements de production et réduit l'utilisation de réactifs en comparaison aux procédés actuels pour effectuer la synthèse de la classe de composé indiquée ci-dessus.