N-苯甲酰基-5-O-(二(4-甲氧基苯基)苯基甲基)-2-脱氧-3-胞苷酸单(2-氯苯基)酯化合物与N,N-二乙基乙胺(1:1) | 85381-24-4

• 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: N-苯甲酰基-5-O-(二(4-甲氧基苯基)苯基甲基)-2-脱氧-3-胞苷酸单(2-氯苯基)酯化合物与N,N-二乙基乙胺(1:1)
• 英文名称: 5'-O-(dimethoxytrityl)-N-benzoyl-2'-deoxycytidine 3'-(o-chlorophenyl phosphate) triethylammonium salt
• 英文别名: 5'-O-(dimethoxytrityl)-N-benzoyl-2'-deoxycytidine 3'-(o-chlorophenyl) phosphate triethylammonium salt；N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-2'-deoxy-3'-cytidylic acid, mono(2-chlorophenyl) ester, compd. with N,N-diethylethanamine (1:1)；[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl] (2-chlorophenyl) hydrogen phosphate;N,N-diethylethanamine
• CAS: 85381-24-4
• 化学式: C₆H₁₅N*C₄₃H₃₉ClN₃O₁₀P
• 分子量: 925.415
• InChiKey: IHCAQPYUATVUIY-BQCABBGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  65
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-苯甲酰基-5-O-(二(4-甲氧基苯基)苯基甲基)-2-脱氧-3-胞苷酸单(2-氯苯基)酯化合物与N,N-二乙基乙胺(1:1) 在 吡啶 、 甲醇 、 苯甲基-2-磺酰三硝基三氮唑 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成
  参考文献：
  名称：

  Improved Synthesis of Trinucleotide Phosphoramidites and Generation of Randomized Oligonucleotide Libraries

  摘要：

  A new method to produce a set of 20 high quality trinucleotide phosphoramidites on a 5-10 g scale each was developed. The procedure starts with condensation reactions of P-components with N-acyl nucleosides, bearing the 3 '-hydroxyl function protected with 2-azidomethylbenzoyl, to give fully protected dinucleoside phosphates 13. Upon cleavage of dimethoxytrityl group from 13, dinucleoside phosphates 16 are initially transformed into trinucleoside diphosphates 19 and then the 2-azidomethylbenzoyl is selectively removed under neutral conditions to generate trinucleoside diphosphates 5 in excellent yield. Subsequent 3 '-phosphitylation affords target trinucleotide phosphoramidites 7. When mutagenic oligonucleotides are synthesized employing mixtures of building blocks 7 as well as following the new synthetic protocol, representative oligonucleotide libraries are generated in good yields.

  DOI：

  10.1080/15257770701426260
• 作为产物：
  描述：

  三乙基碳酸氢铵缓冲液 、 N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷 、 2-氯苯基二氯膦 在 吡啶 、 1H-1,2,3-三氮唑 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 N-苯甲酰基-5-O-(二(4-甲氧基苯基)苯基甲基)-2-脱氧-3-胞苷酸单(2-氯苯基)酯化合物与N,N-二乙基乙胺(1:1)
  参考文献：
  名称：

  Improved Synthesis of Trinucleotide Phosphoramidites and Generation of Randomized Oligonucleotide Libraries

  摘要：

  A new method to produce a set of 20 high quality trinucleotide phosphoramidites on a 5-10 g scale each was developed. The procedure starts with condensation reactions of P-components with N-acyl nucleosides, bearing the 3 '-hydroxyl function protected with 2-azidomethylbenzoyl, to give fully protected dinucleoside phosphates 13. Upon cleavage of dimethoxytrityl group from 13, dinucleoside phosphates 16 are initially transformed into trinucleoside diphosphates 19 and then the 2-azidomethylbenzoyl is selectively removed under neutral conditions to generate trinucleoside diphosphates 5 in excellent yield. Subsequent 3 '-phosphitylation affords target trinucleotide phosphoramidites 7. When mutagenic oligonucleotides are synthesized employing mixtures of building blocks 7 as well as following the new synthetic protocol, representative oligonucleotide libraries are generated in good yields.

  DOI：

  10.1080/15257770701426260

文献信息

• Improved Synthesis of Oligodeoxyribonucleotides by Solid-Phase Phosphotriester Method UtilizingO6-[2-(p-Nitrophenyl)ethyl]-2?-deoxyguanosine Derivatives
  作者：Andr� Chollet、Edgar Ayala、Eric H. Kawashima

  DOI：10.1002/hlca.19840670521

  日期：1984.8.8

  The synthesis of oligodeoxyribonucleotides on a cross-linked polystyrene solid support utilizing stable mono- and dinucleotide phosphotriester building blocks is presented. The use of O6[2-(p-nitrophenyl)ethyl]-2′-deoxyguanosine derivatives yields cleaner DNA fragments by suppressing side reactions. Modifications improving the phosphotriester methodology are presented. The purification methods and

  提出了利用稳定的单核苷酸和二核苷酸磷酸三酯结构单元在交联的聚苯乙烯固体载体上合成寡脱氧核糖核苷酸。使用ö 6 [2-（p通过抑制副反应硝基苯基）乙基] -2'-脱氧鸟苷的产率衍生物吸尘器的DNA片段。提出了改进磷酸三酯方法的修饰。描述了合成寡聚脱氧核糖核苷酸的纯化方法和分析。
• N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride: a novel coupling reagent in the synthesis of oligodeoxyribonucleotides
  作者：S.B. Katti、K.L. Agarwal

  DOI：10.1016/s0040-4039(00)98833-6

  日期：1985.1

  Use of a novel coupling reagent, N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride (BOPDC) in the synthesis of oligodeoxyribonucleotides is described. This reagent allows the synthesis of phosphotriesters in high yields (70–80%) without detectable side reactions. Synthesis of a hexanucleotide, d(A-A-C-C-C-G) is presented as an example.

  描述了一种新颖的偶联剂，N，N-双[2-氧代-3-恶唑烷二基]磷二酰胺基氯化物（BOPDC）在寡聚脱氧核糖核苷酸的合成中的用途。该试剂可以高产率（70-80％）合成磷酸三酯，而没有可检测到的副反应。以六核苷酸d（AACCCG）的合成为例。
• Efficient and flexible access to fully protected trinucleotides suitable for DNA synthesis by automated phosphoramidite chemistry
  作者：Andrea Zehl、Antje Starke、Dieter Cech、Thomas Hartsch、Rainer Merkl、Hans-Joachim Fritz

  DOI：10.1039/cc9960002677

  日期：——

  An efficient synthetic approach to protected trinuclotide phosphoramidites suitable for codon-by-codon synthesis of structural gene combinatorial libraries is described; the procedure rests on the use of pair of orthogonal protecting groups for the two oligomer termini and offers flexibility in the choice of chain elongation direction going from dimer to trimer.

  本文介绍了一种高效的三核苷酸磷酰胺保护合成方法，适用于逐个密码子合成结构基因组合文库；该方法的基础是在两个寡聚体末端使用一对正交的保护基团，并可灵活选择从二聚体到三聚体的链延伸方向。
• Photoinduced deoxyribose C2' oxidation in DNA. Alkali-dependent cleavage of erythrose-containing sites via a retroaldol reaction
  作者：Hiroshi Sugiyama、Yasushi Tsutsumi、Kenzo Fujimoto、Isao Saito

  DOI：10.1021/ja00064a004

  日期：1993.6

  Photoreactions of various 5-iodouracil-((I)U)-containing oligonucleotides have been investigated. It was found that d(GCA(I)UGC)2 undergoes a competitive C1' and C2' oxidation at the 5' side of the (I)U residue to give deoxyribonolactone-containing hexamer 1 and erythrose-containing hexamer 2, respectively. Upon beating under alkaline conditions, erythrose-containing hexamer 2 was shown to undergo a remarkably facile retroaldol reaction to give two fragments, both having phosphoroglycoaldehyde termini in high yields. On the basis of the chemical reactivity of 2, a new specific method for detection of the erythrose-containing sites resulting from deoxyribose C2' oxidation in DNA was devised. Erythrose-containing sites were prepared by photoirradiation of duplex (I)U-containing 13 mer 5'-d(CG(I)UGT(I)UTA(I)UAC(I)UG)-3'/5'-d(CAGTATAAACACG)-3'. After photoirradiation, the reaction mixture was treated with hot alkali and NaBH4 and then subjected to enzymatic digestion. HPLC analysis of the digested mixture revealed the formation of modified mononucleotides 25-28, allowing the quantification of the erythrose-containing sites being produced at the 5' side of all four (I)U residues of the 13 mer. These results indicate that this method can be used for the detection and quantification of erythrose-containing sites resulting from deoxyribose C2' oxidation in DNA.
• Specific detection of C-4' hydroxylated abasic sites generated by bleomycin and neocarzinostatin in DNA
  作者：Hiroshi Sugiyama、Hiroshi Kawabata、Tsuyoshi Fujiwara、Yukihiro Dannoue、Isao Saito

  DOI：10.1021/ja00169a037

  日期：1990.6