5'-O-((2-cyanoethoxy)-(5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl)phosphorothioyl)thymidine | 124716-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-((2-cyanoethoxy)-(5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl)phosphorothioyl)thymidine
• 英文别名: 5'-O-(4,4'-dimethoxytrityl)dithymidilyl phosphorothioate；3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphinothioyl]oxypropanenitrile
• CAS: 124716-09-2
• 化学式: C₄₄H₄₈N₅O₁₃PS
• 分子量: 917.931
• InChiKey: VBOOBSKJTYLOFH-DFMHVPIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  64
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  249
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 5'-O-((2-cyanoethoxy)-(5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl)phosphorothioyl)thymidine 生成 3-[[(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  Improved Impurity Profile of Phosphorothioate Oligonucleotides Through the Use of Dimeric Phosphoramidite Synthons

  摘要：

  Phosphorothioate oligonucleotides synthesized through assembly of dimeric phosphoramidite synthons show a significantly improved impurity profile compared to oligomers synthesized through coupling of standard monomer phosphoramidites. A greater than 70% reduction of the (n-1)-mer population and a ca. 50% reduction of phosphodiester linkages has been achieved.

  DOI：

  10.1080/07328319708006244
• 作为产物：
  描述：

  保护胸苷 在 N-甲基吗啉 、 1H-1,2,4-三唑 、 sulfur 、 一水合肼 、 三氯化磷 作用下， 以 四氢呋喃 、 吡啶 、 溶剂黄146 为溶剂， 反应 3.67h， 生成 5'-O-((2-cyanoethoxy)-(5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl)phosphorothioyl)thymidine
  参考文献：
  名称：

  Investigation of a Facile Synthetic Method for Phosphorothioate Dimer Synthons In Oligonucleotide Phosphorothioates Synthesis

  摘要：

  A facile synthetic method of a phosphorothioate dimer block was investigated. Dinucleoside phosphite triester intermediates were obtained in one-pot synthesis by the coupling of a protected nucleoside bearing free 5'-OH and a protected nucleoside bearing free 3'-OH in the presence of phosphorous trichloride (PCl3) and 1,2,4-triazole. The intermediates were easily sulfurized to afford the desired phosphorothioate dimer blocks in 33-64% overall yields.

  DOI：

  10.1080/15257770008033035

文献信息

• アルコキシフェニル誘導体、ヌクレオシド保護体およびヌクレオチド保護体、オリゴヌクレオチド製造方法、ならびに、置換基除去方法
  申请人：藤本化学製品株式会社

  公开号：JP2020011932A

  公开（公告）日：2020-01-23

  【課題】従来よりも簡易迅速な液相合成法によるオリゴヌクレオチドの合成が可能となるアルコキシフェニル誘導体、前記アルコキシフェニル誘導体が結合したヌクレオシド保護体およびヌクレオチド保護体、それらを用いたオリゴヌクレオチドの製造方法、並びに該アルコキシフェニル誘導体部分の選択的な除去方法等の提供。【解決手段】一般式（１）で表される化合物またはその誘導体。（式中、Ｒは夫々独立して置換／非置換のＣ１０〜４０のアルキル；ｍは１〜５の整数；ｍが２以上の場合、複数存在するＲＯは異なっていてもよい；Ｘは、Ｏ、Ｓ、ＮＨ又はＮＲＮ；ｎは１〜４の整数；ＲＮは置換／非置換のＣ１〜６のアルキル）【選択図】なし

  这项技术使得通过比传统更简便迅速的液相合成方法合成寡核苷酸成为可能，提供了含有醚基苯基衍生物的能够结合的核苷保护基和核苷酸保护基，以及利用它们制备寡核苷酸的方法，还包括选择性去除该醚基苯基衍生物部分的方法等。解决方案是通过一般式（1）所示的化合物或其衍生物实现的。（其中，R分别是独立的取代/未取代的C10-40烷基；m是1-5的整数；当m大于2时，可能存在多个不同的RO；X是O、S、NH或NRN；n是1-4的整数；RN是取代/未取代的C1-6烷基）【选择图】无
• Improved Impurity Profile of Phosphorothioate Oligonucleotides Through the Use of Dimeric Phosphoramidite Synthons
  作者：Achim H. Krotz、Patrick Klopchin、Douglas L. Cole、Vasulinga T. Ravikumar

  DOI：10.1080/07328319708006244

  日期：1997.7

  Phosphorothioate oligonucleotides synthesized through assembly of dimeric phosphoramidite synthons show a significantly improved impurity profile compared to oligomers synthesized through coupling of standard monomer phosphoramidites. A greater than 70% reduction of the (n-1)-mer population and a ca. 50% reduction of phosphodiester linkages has been achieved.
• Investigation of a Facile Synthetic Method for Phosphorothioate Dimer Synthons In Oligonucleotide Phosphorothioates Synthesis
  作者：Takanori Miyashita、Kohei Yamada、Kazuhiko Kondo、Kenya Mori、Kazuo Shinozuka

  DOI：10.1080/15257770008033035

  日期：2000.5

  A facile synthetic method of a phosphorothioate dimer block was investigated. Dinucleoside phosphite triester intermediates were obtained in one-pot synthesis by the coupling of a protected nucleoside bearing free 5'-OH and a protected nucleoside bearing free 3'-OH in the presence of phosphorous trichloride (PCl3) and 1,2,4-triazole. The intermediates were easily sulfurized to afford the desired phosphorothioate dimer blocks in 33-64% overall yields.
• Synthesis of Dimer Phosphoramidite Synthons for Oligodeoxyribonucleotide Phosphorothioates Using Diethyldithiocarbonate disulfide as an Efficient Sulfurizing Reagent
  作者：Alessandra Eleuteri、Zacharia S. Cheruvallath、Daniel C. Capaldi、Douglas L. Cole Vasulinga、T. Ravikumar

  DOI：10.1080/07328319908044844

  日期：1999.8

  An efficient solution phase synthesis of deoxyribonucleoside phosphorothioate dimers utilizing phosphoramidite approach is described. Diethyldithiocarbonate disulfide (DDD) was found to be an efficient sulfurizing reagent in the conversion of phosphite triesters to phosphorothioate triesters.