5'-O-dimethoxytrityl-4-N-p-toluenesulfonyl-2'-deoxycytidine | 147139-43-3

• 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-dimethoxytrityl-4-N-p-toluenesulfonyl-2'-deoxycytidine
• 英文别名: N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]-4-methylbenzenesulfonamide
• CAS: 147139-43-3
• 化学式: C₃₇H₃₇N₃O₈S
• 分子量: 683.782
• InChiKey: BWRAQNNDBBAIEJ-VUHKNJSWSA-N

物化性质

• 沸点：
  824.8±75.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-dimethoxytrityl-4-N-p-toluenesulfonyl-2'-deoxycytidine 在 吡啶 作用下， 反应 17.08h， 生成 N-[3-[4-[3-[[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]amino]propyl-(2,2,2-trifluoroacetyl)amino]butyl-(2,2,2-trifluoroacetyl)amino]propyl]-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Synthesis of A Polyaminooligonucleotide Combinatorial Library

  摘要：

  A new method of synthesis of phosphoramidite of 2'-deoxycytydine carrying a protected spermine moiety at N-4 position is described. A model oligodeoxyribonucleotide containing the specified nucleoside unit has been synthesised. A synthesis of a polyaminooligonucleotide combinatorial library was carried out. The analysis of the above library clearly shows that the presence of spermine moieties in oligodeoxyribonucleotides increases stability of their duplexes.

  DOI：

  10.1080/07328319808004725
• 作为产物：
  描述：

  N-{1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-4-methyl-benzenesulfonamide 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 5'-O-dimethoxytrityl-4-N-p-toluenesulfonyl-2'-deoxycytidine
  参考文献：
  名称：

  Phototriggering of Caged Fluorescent Oligodeoxynucleotides

  摘要：

  We describe a synthetic route for incorporating a photocleavable (PC) DABSYL moiety and fluorescein at adjacent cytidines in the middle of a 25-mer oligodeoxynucleotide. In hybridization studies, both fluorescein and the photocleavable DABSYL reduced the T-m about 6 degreesC separately. UV irradiation (355 nm, 2 min) removed the PC-DABSYL moiety, which increased the fluorescence intensity 51-fold and restored the melting temperature. Caged fluorescent oligodeoxynucleotides (CFOs) will allow many DNA processes to be controlled with light.

  DOI：

  10.1021/ol047729n

文献信息

• Functionalized carrier materials for the simultaneous synthesis and
  申请人：Boehringer Mannheim GmbH

  公开号：US05574141A1

  公开（公告）日：1996-11-12

  The synthesis and use of polymeric carriers is described which are loaded with nucleic acid building blocks which in turn contain labelling groups or precursors thereof. The polymeric carrier loaded in this way serves as a solid or liquid phase for the assembly of oligonucleotides which can be used as primers for template-dependent enzymatic nucleic acid syntheses such as for example in sequencing analysis according to Sanger and co-workers or in the polymerase chain reaction (PCR).

  描述了合成和使用聚合物载体，其中装载有含有标记基团或其前体的核酸构建块。这种以这种方式装载的聚合物载体可用作寡核苷酸的组装的固体或液相，这些寡核苷酸可用作模板依赖性酶催化核酸合成的引物，例如根据桑格及其合作者的测序分析或聚合酶链反应（PCR）中使用。
• PRIMER FÜR MATRIZENABHÄNGIGE ENZYMATISCHE NUKLEINSÄURESYNTHESEN
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0600965B1

  公开（公告）日：1998-02-18
• US5574141A
  申请人：——

  公开号：US5574141A

  公开（公告）日：1996-11-12
• Phototriggering of Caged Fluorescent Oligodeoxynucleotides
  作者：Tang、Ivan J. Dmochowski

  DOI：10.1021/ol047729n

  日期：2005.1.1

  We describe a synthetic route for incorporating a photocleavable (PC) DABSYL moiety and fluorescein at adjacent cytidines in the middle of a 25-mer oligodeoxynucleotide. In hybridization studies, both fluorescein and the photocleavable DABSYL reduced the T-m about 6 degreesC separately. UV irradiation (355 nm, 2 min) removed the PC-DABSYL moiety, which increased the fluorescence intensity 51-fold and restored the melting temperature. Caged fluorescent oligodeoxynucleotides (CFOs) will allow many DNA processes to be controlled with light.
• Synthesis of A Polyaminooligonucleotide Combinatorial Library
  作者：Wojciech. T. Markiewicz、Przemyslaw Godzina、Maria Markiewicz、Anna Astriab

  DOI：10.1080/07328319808004725

  日期：1998.9

  A new method of synthesis of phosphoramidite of 2'-deoxycytydine carrying a protected spermine moiety at N-4 position is described. A model oligodeoxyribonucleotide containing the specified nucleoside unit has been synthesised. A synthesis of a polyaminooligonucleotide combinatorial library was carried out. The analysis of the above library clearly shows that the presence of spermine moieties in oligodeoxyribonucleotides increases stability of their duplexes.