膦酸,1,2-乙二基二(磷羧基甲基)亚氨基-3,1-丙二基次氮基<三价氮基>二(亚甲基)四-,盐钠 | 195375-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 膦酸,1,2-乙二基二(磷羧基甲基)亚氨基-3,1-丙二基次氮基&lt三价氮基&gt二(亚甲基)四-,盐钠
• 英文名称: 3'-NH-trityl-3'-aminothymidine 5'-O-cyanoethyl-N,N-diisopropylaminophosphoramidite
• 英文别名: 3'-aminotrityl-3'-deoxythymidine-5'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite；3-[[di(propan-2-yl)amino]-[[(2S,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-(tritylamino)oxolan-2-yl]methoxy]phosphanyl]oxypropanenitrile
• CAS: 195375-68-9
• 化学式: C₃₈H₄₆N₅O₅P
• 分子量: 683.787
• InChiKey: DVCDDVDHERUJQD-KBUNAWGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  膦酸,1,2-乙二基二(磷羧基甲基)亚氨基-3,1-丙二基次氮基<三价氮基>二(亚甲基)四-,盐钠 生成
  参考文献：
  名称：

  Oligonucleotide N3′→P5′ thiophosphoramidates: synthesis and properties

  摘要：

  Uniformly modified oligonucleotides with a novel sugar-phosphate backbone containing internucleoside 3'-NHP(O)(S-)O-5' linkages were synthesized. These oligonucleotides were found to retain the high RNA binding affinity of the parent oligonucleotide N3'-->P5' phosphoramidates and to exhibit a much higher acid stability. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01584-1
• 作为产物：
  描述：

  3'-氨基-2',3'-双脱氧胸苷 在 吡啶 、 二异丙基铵盐四氮唑 、 三乙胺 作用下， 生成 膦酸,1,2-乙二基二(磷羧基甲基)亚氨基-3,1-丙二基次氮基<三价氮基>二(亚甲基)四-,盐钠
  参考文献：
  名称：

  寡核苷酸 N3′⇉P5′ 磷酸酯砌块的新方法

  摘要：

  开发了 3'-氨基核苷的 5'-亚磷酰胺的新合成方法。该方法依赖于使用 3'-amino-2',3'-dideoxy 核苷作为关键起始材料。最终的亚磷酰胺产物是通过 2-3 步高效化学转化获得的，使用选择性地将正交保护基团引入 3'-氨基核苷糖和碱基部分。

  DOI：

  10.1081/ncn-200060068

文献信息

• N3‘→P5‘ Oligodeoxyribonucleotide Phosphoramidates:  A New Method of Synthesis Based on a Phosphoramidite Amine-Exchange Reaction
  作者：Jeffrey S. Nelson、Karen L. Fearon、Mark Q. Nguyen、Sarah N. McCurdy、Jeff E. Frediani、Michael F. Foy、Bernard L. Hirschbein

  DOI：10.1021/jo970801t

  日期：1997.10.1

  for the synthesis of N3'-->P5' phosphoramidate oligodeoxynucleotides is demonstrated. Described herein is the synthesis of the monomers utilized in the phosphoramidite amine-exchange process and the experimental details pertaining to this new mode of chain assembly. The phosphoramidite amine-exchange method generates coupling yields in the 92-95% range per cycle and further enables the synthesis of chimeric

  展示了一种合成N3'-> P5'氨基磷酸亚氨基寡脱氧核苷酸的新方法。本文描述了亚磷酰胺交换反应中所用单体的合成以及与这种新的链组装方式有关的实验细节。亚磷酰胺交换法在每个循环中产生的偶联收率在92-95％的范围内，并且无需进行仪器修饰即可合成嵌合的氨基磷酸酯/磷酸二酯或氨基磷酸酯/硫代磷酸酯寡核苷酸。
• Synthesis of protected 3'-amino nucleoside monomers
  申请人：Gryaznov M. Sergei

  公开号：US20060009636A1

  公开（公告）日：2006-01-12

  Orthogonally protected 3′-amino nucleoside monomers and efficient methods for their synthesis are described. The methods employ selective protection of the 3′-amino group in the presence of the unprotected nucleoside base.

  正交保护的3′-氨基核苷单体及其高效合成方法被描述。这些方法在未保护的核苷碱基存在下，采用对3′-氨基基团的选择性保护。
• Synthesis of Phosphorodiamidate Oligonucleotide Dimers
  作者：Jennifer Albaneze-Walker、Gregor Urbanietz、Andras Horvath、Stefano Lancianesi、Alejandro Gimenez Molina、Thomas De Vijlder、Mattijs Baeten、Martine Canters

  DOI：10.1021/acs.joc.2c01582

  日期：2022.10.7

  eliminates acrylonitrile to generate the coupled dimer P(V) product. The vulnerable phosphite triester intermediate is bypassed entirely, making the methodology very suitable to solution-phase synthesis. This new coupling protocol requires no protection of the 5′-OH function and provides a new method of installing internucleosidic phosphorodiamidate bonds with near quantitative yields.

  叠氮基核苷通过初始亚氨基正膦与亚磷酰胺偶联，从而消除丙烯腈以生成偶联二聚体 P(V) 产物。易受攻击的亚磷酸三酯中间体被完全绕过，使该方法非常适合溶液相合成。这种新的偶联方案不需要保护 5'-OH 功能，并提供了一种安装核苷间磷酸二酰胺键的新方法，产率接近定量。
• TELOMERASE-INHIBITORY ENA OLIGONUCLEOTIDE
  申请人：Sankyo Company, Limited

  公开号：EP1783216A1

  公开（公告）日：2007-05-09

  A compound represented by general formula:         E1-B1-B2-B3-B4-E2     (I) (wherein E1 represents a group represented by the formula R1- or the like; E2 represents a group represented by the formula -B7-R2 or the like; B4, B5, and B8 are identical or different, and each represents Tp or the like; B1, B2, B3, and B12 are identical or different, and each represents Gp or the like; B 16 represents Cp or the like; and B6, B10, B14, and B18 are identical or different, and each represents Ap or the like) or a pharmacologically acceptable salt thereof, inhibits the action of telomerase and is effective in treating diseases in which telomerase is involved.

  由通式代表的化合物： E1-B1-B2-B3-B4-E2 (I) (其中 E1 代表由式 R1-或类似物代表的基团；E2 代表由式 -B7-R2 或类似物代表的基团；B4、B5 和 B8 相同或不同，且各自代表 Tp 或类似物；B1、B2、B3 和 B12 相同或不同，且各自代表 Gp 或类似物；B16代表Cp或类似物；以及B6、B10、B14和B18相同或不同，且各自代表Ap或类似物）或其药理学上可接受的盐，可抑制端粒酶的作用，对治疗端粒酶参与的疾病有效。
• A new approach to oligonucleotide N3′→P5′ phosphoramidate building blocks
  作者：Daria Zielinska、Krisztina Pongracz、Sergei M. Gryaznov

  DOI：10.1016/j.tetlet.2006.04.100

  日期：2006.6

  A new synthetic approach to 5'-phosphoramidites of 3'-aminonucleosides was developed. The methodology relics upon the use of 3'-amino-2',3'-dideoxynucleosides as the key starting materials. The final products were obtained in high yields via 2-3-step processes using selective introduction of orthogonal protective groups to the 3'-aminonucleoside sugar and base moieties. (c) 2006 Elsevier Ltd. All rights reserved.