O-(5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-2-deoxyadenosin-3'-yl) N,N-diisopropylfluorophosphoramidite | 162611-38-3

• 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: O-(5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-2-deoxyadenosin-3'-yl) N,N-diisopropylfluorophosphoramidite
• 英文别名: N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[di(propan-2-yl)amino]-fluorophosphanyl]oxyoxolan-2-yl]purin-6-yl]benzamide
• CAS: 162611-38-3；162611-39-4；171081-09-7
• 化学式: C₄₄H₄₈FN₆O₆P
• 分子量: 806.874
• InChiKey: OSBCWVBXMJWPGX-CNGLVTPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O-(5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-2-deoxyadenosin-3'-yl) N,N-diisopropylfluorophosphoramidite 在 四氮唑 、 sulfur 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 Thiophosphorofluoridic acid O-{(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl} ester O'-(2-cyano-ethyl) ester
  参考文献：
  名称：

  First Synthesis of Nucleosidyl Phosphorofluoridothioates and a Convenient Synthesis of Nucleosidyl Phosphorofluoridates

  摘要：

  通过核苷基磷酰胺氟化物RO-P(NPri2)F，首次合成了3′-或5′-核苷基磷酰氟硫代酯RO-P(S)(OH)F。通过类似的简便方法，制备了3′-或5′-核苷基磷酰氟酯RO-P(O)(OH)F。

  DOI：

  10.1246/cl.1995.727
• 作为产物：
  描述：

  N6-苯甲酰基-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧腺苷 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 O-(5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-2-deoxyadenosin-3'-yl) N,N-diisopropylfluorophosphoramidite
  参考文献：
  名称：

  Synthesis and Characterization of Phosphate-modified DNA-Dimers with Fluorine as an uncharged Ligand

  摘要：

  The potential of the dinucleosidylphosphorofluoridates dCp(F)dG and dAp(F)dT is described. Side products of the phosphoramidite coupling reaction are synthesized and characterized by P-31-NMR-spectroscopy.

  DOI：

  10.1080/07328319708002957

文献信息

• Synthesis of phosphorofluoridates and phosphorofluoridothioates via the phosphoramidite approach
  作者：Wojciech Dabkowski、Izabela Tworowska

  DOI：10.1039/b413552k

  日期：——

  We present a very efficient synthetic procedure leading to the phosphorofluoridates RO-P(O)(OH)F 1 or phosphorofluoridothioates RO-P(S)(OH)F 2, which is based on the intermediary of fluorophosphoramidites (RO)P(F)NiPr25 [R = 9-(hydroxyethyloxymethyl)guaninyl), 3′azido-3′deoxythymidinyl, thymidinyl, anhydrothymidinyl, cholesteryl, N6-benzoyl-5′-O-(4,4′-dimethoxytrityl)-2′-deoxyadenosinyl]. The activation of the amino group was performed with trimethylchlorosilane (TMCS).

  我们介绍了一种非常高效的合成方法，能够制备出磷氟酸盐RO-P(O)(OH)F 1或磷氟硫酸盐RO-P(S)(OH)F 2，其方法基于氟磷酰胺中间体(RO)P(F)NiPr25 [R = 9-(羟乙氧甲基)鸟嘌呤基、3′叠氮-3′脱氧胸苷基、胸苷基、脱水胸苷基、胆固醇基、N6-苯甲酰-5′-O-(4,4′-二甲氧基三苯甲基)-2′-脱氧腺苷基]。氨基的活化采用三甲基氯硅烷（TMCS）完成。
• Trimethylchlorosilane: a novel activating reagent in nucleotide synthesis via the phosphoramidite route
  作者：Wojciech Dabkowski、Izabela Tworowska、Jan Michalski、Friedrich Cramer

  DOI：10.1039/a701924f

  日期：——

  Trimethylchlorosilane (TMSCl) is a remarkably efficient activator in the reaction of phosphorus(III) amides with nucleosides to give phosphorus(III) esters in excellent yield.

  在磷(III)酰胺与核苷反应生成磷(III)酯的过程中，三甲基氯硅烷（TMSCl）是一种非常有效的活化剂，收率极高。
• Diastereoisomerically pure dinucleosidylphosphorofluoridites and their application in stereospecific synthesis of dinucleosidylphosphorofluoridothionates
  作者：Wojciech Dąbkowski、Izabela Tworowska、Jan Michalski、Fritz Cramer

  DOI：10.1039/c39950001435

  日期：——

  Dinucleosidylphosphorofluoridites with dA(Bz), dC(Bz) or dT at the 3′-end and dT at the 5′-end are synthesised, separated into their diastereoisomers and shown to be converted stereospecifically into the corresponding phosphorofluoridothionates high hydrolytic stability.

  合成了 3′端为 dA(Bz)、dC(Bz) 或 dT 和 5′端为 dT 的二核苷基磷酰亚胺，并将其分离成非对映异构体，结果表明它们能立体定向地转化为相应的磷酰亚胺硫酸盐，具有很高的水解稳定性。
• Synthesis of 2′-deoxynucleosid-3′-yl-N,N-diisopropylaminophosphorfluoridites. A new class of stable PIII nucleotides containing a PF bond
  作者：Wojciech Dabkowski、Izabela Tworowska

  DOI：10.1016/0040-4039(94)02403-x

  日期：1995.2

  A new methodology based on phosphitylating reagents containing 4-nitrophenoxy leaving group has been employed to synthesize stable 5'-O-(4,4'-dimethoxytrityl)nucleosid-3'-yl-N,N-diisopropylaminophosphorfluoridites Ia-d.
• A simple and efficient synthesis of nucleotides containing 5′-S- or 3′-S-phosphorothioate linkage.
  作者：W. Dabkowski、M. Michalska、I. Tworowska

  DOI：10.1080/07328319808004695

  日期：1998.9

  A new efficient synthesis procedure leading to the nucleotide containing 5'-S or 3'-S-phosphorothioate linkage will be presented. The tittle compounds were prepared in the reaction anhydronucleoside with nucleoside phosphorodithioates. The second way is based on phosphitylation reaction using the nucleosidylphosphorofluoridites.