N6-Benzoyl-9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine | 116597-12-7

• 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-9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine
• 英文别名: N⁶-benzoyl-9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine；N6-Benzoyl-9-(5-O-benzoyl-2-deoxy-beta-D-threo-pentofuranosyl)adenine；[(2R,3R,5R)-5-(6-benzamidopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 116597-12-7
• 化学式: C₂₄H₂₁N₅O₅
• 分子量: 459.461
• InChiKey: INUFEIRTCLFJBN-GUDVDZBRSA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N6-Benzoyl-9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine 在 氨 作用下， 以 甲醇 为溶剂， 生成 3'-叠氮-2',3'-双脱氧腺苷
  参考文献：
  名称：

  Anchimeric assistance of a 5'-O-carbonyl function for inversion of configuration at the 3'-carbon atom of 2'-deoxyadenosine. Synthesis of 3'-azido-2',3'-dideoxyadenosine and 3'-azido-2',3'-dideoxyinosine

  摘要：

  DOI：

  10.1021/jo00256a027
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 三氟甲磺酸酐 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 N6-Benzoyl-9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine
  参考文献：
  名称：

  二硫骨架核酸的研究：第1部分，3',5'-二硫-2'-脱氧腺苷的高效合成

  摘要：

  建立了一个有效的程序来合成 3',5'-二硫-2'-脱氧腺苷，从 2'-脱氧腺苷开始，分五步，总产率为 33%。在该程序中，关键中间体9通过两次3'-构型反转的两次SN 2 反应合成，然后通过在一锅中去除三个酰基将其脱保护为标题化合物。

  DOI：

  10.1055/s-2004-834809

文献信息

• 3'-(2')-amino or thiol-modified, fluorescent dye-coupled
  申请人：Hoechst Aktiengesellschaft

  公开号：US05659025A1

  公开（公告）日：1997-08-19

  The OH group located in the 3' and/or 2' position of a nucleoside, nucleotide or oligonucleotide is derivatized to an amino or thiol group and subsequently a fluorescent dye is coupled thereto. The resulting 3'- and/or 2'-amino- and thiol-modified nucleosides, nucleotides and oligonucleotides can then be used for the synthesis of complementary strands in the presence of a template strand or of oligonucleotides and for the detection of genetic material. They have the advantage that the fluorescent label need no longer be attached to the 5' end of the oligonucleotide or to the nucleobase, and thus need not be introduced during the chemical synthesis as in labeling techniques hitherto known, while the known and conventional methods have the disadvantage that only a few polymerases can be employed for the synthesis, the acceptance of the triphosphates by the polymerases diminishes and, moreover, a large substrate excess is necessary.

  位于核苷酸，核苷酸或寡核苷酸的3'和/或2'位置的OH基团被衍生为氨基或巯基，随后荧光染料与其偶联。由此产生的3'-和/或2'-氨基和巯基修饰的核苷酸，核苷酸和寡核苷酸可以在模板链或寡核苷酸存在下用于合成互补链和检测遗传物质。它们的优点是，荧光标记不再需要连接到寡核苷酸的5'端或核碱基上，因此不需要像已知的标记技术中那样在化学合成过程中引入，而已知的传统方法的缺点是只有少数聚合酶可以用于合成，聚合酶对三磷酸盐的接受度降低，此外，需要大量底物过剩。
• 3'-(2')-amimo- or thiol-modified, fluorescent dye-coupled nucleosides,
  申请人：Hoechst Aktiengesellschaft

  公开号：US05668269A1

  公开（公告）日：1997-09-16

  3'-(2')-Amino- or thiol-modified, fluorescent dye-coupled nucleosides, nucleotides and oligonucleotides, and a process for the preparation and the use thereof. The OH group located in the 3' and/or 2' position of a nucleoside, nucleotide or oligonucleotide is derivatized to an amino or thiol group and subsequently a fluorescent dye is coupled thereto. The resulting 3'- and/or 2'-amino- and thiol-modified nucleosides, nucleotides and oligonucleotides can then be used for the synthesis of complementary strands in the presence of a template strand or of oligonucleotides and for the detection of genetic material. They have the advantage that the fluorescent label need no longer be attached to the 5' end of the oligonucleotide or to the nucleobase, and thus need not be introduced during the chemical synthesis as in labeling techniques hitherto known, while the known and conventional methods have the disadvantage that only a few polymerases can be employed for the synthesis, the acceptance of the triphosphates by the polymerases diminishes and, moreover, a large substrate excess is necessary.

  3'-(2')-氨基或巯基修饰的荧光染料偶联核苷、核苷酸和寡核苷酸，以及其制备和使用的方法。将位于核苷、核苷酸或寡核苷酸的3'和/或2'位置上的OH基团衍生成氨基或巯基，然后将荧光染料偶联到其上。得到的3'-和/或2'-氨基和巯基修饰的核苷、核苷酸和寡核苷酸可以在模板链或寡核苷酸存在的情况下用于合成互补链和检测遗传物质。它们的优点是荧光标记不再需要附加到寡核苷酸的5'端或核碱基上，因此不像迄今已知的标记技术中那样需要在化学合成过程中引入，而已知的传统方法的缺点是只有少数聚合酶可用于合成，聚合酶对三磷酸盐的接受能力降低，此外还需要大量的底物过量。
• 3'(2')-amino- or thiol-modified, fluorescent dye-coupled nucleosides,
  申请人：Hoechst Aktiengesellschaft

  公开号：US05679785A1

  公开（公告）日：1997-10-21

  3'-(2')-Amino- or thiol-modified, fluorescent dye-coupled nucleosides, nucleotides and oligonucleotides, and a process for the preparation and the use thereof The OH group located in the 3' and/or 2' position of a nucleoside, nucleotide or oligonucleotide is derivatized to an amino or thiol group and subsequently a fluorescent dye is coupled thereto. The resulting 3'- and/or 2'-amino- and thiol-modified nucleosides, nucleotides and oligonucleotides can then be used for the synthesis of complementary strands in the presence of a template strand or of oligonucleotides and for the detection of genetic material. They have the advantage that the fluorescent label need no longer be attached to the 5' end of the oligonucleotide or to the nucleobase, and thus need not be introduced during the chemical synthesis as in labeling techniques hitherto known, while the known and conventional methods have the disadvantage that only a few polymerases can be employed for the synthesis, the acceptance of the triphosphates by the polymerases diminishes and, moreover, a large substrate excess is necessary.

  3'-(2')-氨基或巯基修饰的荧光染料偶联的核苷、核苷酸和寡核苷酸，以及其制备和使用方法。 在核苷、核苷酸或寡核苷酸的3'和/或2'位置上的OH基团被衍生为氨基或巯基，随后与荧光染料偶联。所得的3'-和/或2'-氨基和巯基修饰的核苷、核苷酸和寡核苷酸可用于在模板链或寡核苷酸存在下合成互补链和检测遗传物质。它们的优点是荧光标记不再需要附加在寡核苷酸的5'末端或核碱基上，因此不需要像已知的标记技术中那样在化学合成过程中引入，而已知和传统的方法的缺点是只能使用少数聚合酶进行合成，聚合酶对三磷酸盐的接受度降低，此外还需要大量底物过剩。
• Solid phase synthesis of oligonucleotide N3'-P5' phosphoramidates
  申请人：Lynx Therapeutics, Inc.

  公开号：US05824793A1

  公开（公告）日：1998-10-20

  The invention provides a method of synthesizing oligonucleotide N3'.fwdarw.P5' phosphoramidates using an amine-exchange reaction of phosphoramidites in which a deprotected 3'-amino group of a solid phase supported oligonucleotide chain is exhanged 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.

  本发明提供了一种合成寡核苷酸N3'.fwdarw.P5'磷酰胺酯的方法，使用磷酰胺酯的胺交换反应，在该反应中，固相支持的寡核苷酸链的去保护3'-氨基基团被交换为一个具有受保护的3'-氨基基团的进入单体的5'-磷酰胺酯的氨基部分。然后，将产生的核苷间磷酰胺酯酯键氧化，形成稳定的受保护磷酰胺酯酯键。本发明的方法大大提高了产物收率，并减少了目前可用于合成上述类化合物的方法中的试剂使用。
• Synthons for synthesis of oligonucleotide N3-P5 phosphoramidates
  申请人：Lynx Therapeutics, Inc.

  公开号：US05859233A1

  公开（公告）日：1999-01-12

  The invention provides a method of synthesizing oligonucleotide N3'.fwdarw.P5' phosphoramidates using an amine-exchange reaction of phosphoramidites in which a -deprotected 3'-amino group of a solid phase supported oligonucleotide chain is exhanged 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.

  本发明提供了一种合成寡核苷酸N3'.fwdarw.P5'磷酰胺酰胺的方法，使用磷酰胺酰胺的胺交换反应，在该反应中，固相支持的寡核苷酸链的去保护的3'-氨基基团被交换为一个具有保护的3'-氨基基团的进入单体的5'-磷酰胺酰胺的氨基部分。然后，将得到的核苷酸间磷酰胺酰胺键氧化形成稳定的保护磷酰胺酰胺键。本发明的方法大大提高了产物收率，并减少了合成上述类化合物的当前可用方法所需的试剂用量。