3'-O-(4,4'-dimethoxytrityl)-5'-formylthymidine | 179178-38-2

• 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: 3'-O-(4,4'-dimethoxytrityl)-5'-formylthymidine
• 英文别名: (2S,3S,5R)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-2-carbaldehyde
• CAS: 179178-38-2
• 化学式: C₃₁H₃₀N₂O₇
• 分子量: 542.588
• InChiKey: SBKWBJBCSZFNIH-UPRLRBBYSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-O-(4,4'-dimethoxytrityl)-5'-formylthymidine 在 吡啶 、 咪唑 、 sodium hydroxide 、 甲基溴化镁 、 氨 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 175.5h， 生成 N-[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-2,2,2-trifluoro-acetamide
  参考文献：
  名称：

  含4'- C-取代胸苷的寡脱氧核苷酸的合成与评价

  摘要：

  将4'- C-羟基甲基胸苷转化为4'- C-甲氧基甲基胸苷和4'- C-氨基甲基胸苷，通过亚磷酰胺化学将其掺入寡脱氧核苷酸中。修饰的寡核苷酸表现出优异的杂交性，并且对蛇毒磷酸二酯酶的稳定性显着提高。

  DOI：

  10.1016/0040-4039(96)01432-3
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 吡啶 、 四丁基氟化铵 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 13.0h， 生成 3'-O-(4,4'-dimethoxytrityl)-5'-formylthymidine
  参考文献：
  名称：

  4'-Epi-DNA：一种包含4'-羟甲基-α-l-二甲苯基胸腺嘧啶核苷的DNA模仿物，具有类似RNA的紧凑骨架

  摘要：

  摘要首次报道了含有3'→5''键的C4'-epi-DNA的合成。单体的晶体结构研究表明，尽管在这种情况下二面角O3'-C3'-C4'-C5''与RNA相似，但糖构象仍与DNA相似。本说明中报道了在DNA中这种主链构型对其与cDNA和RNA结合的影响的研究。图形概要

  DOI：

  10.1080/15257770.2016.1202963

文献信息

• Nucleoside 5′-C-phosphonates: reactivity of the α-hydroxyphosphonate moiety
  作者：Šárka Králíková、Miloš Buděšínký、Milena Masojídková、Ivan Rosenberg

  DOI：10.1016/j.tet.2006.03.008

  日期：2006.5

  We found that various dialkyl phosphites, dialkyl trimethylsilyl phosphites, and tris-trimethylsilyl phosphite reacted smoothly with nucleoside 5'-aldehydes to afford epimeric nucleoside 5'-C-phosphonates in high yields. A number of these compounds in both the 2'-deoxyribo and ribo series were prepared. In the case of 2'-deoxythymidine-5'-aldehyde, a thorough study was made on the influence of the 5'-hydroxyl protecting group, type of phosphite, base, and solvent, on the yield and epimeric ratio of the resulting 5'-hydroxyphosphonates. Partial stereoselectivity in favour of either R or S epimers was observed. An attempt to transform the alpha-hydroxyl of the phosphonate moiety into a halo or azido moiety was not Successful. Only intramolecular substitution reaction of the mesyloxy group for an alkoxy residue of the 2-hydroxyethyl ester took place in a low yield. (c) 2006 Elsevier Ltd. All rights reserved.
• 4′-Epi-DNA: A DNA Mimic Containing 4′-hydroxymethyl-α-<scp>l</scp>-Xylo-Thymidine with Compact Backbone like RNA
  作者：Seema Bagmare、Vedavati G. Puranik、Moneesha Fernandes、Vaijayanti A. Kumar

  DOI：10.1080/15257770.2016.1202963

  日期：2016.9

  ABSTRACT Synthesis of C4′-epi-DNA containing 3′→ 5″ linkages is reported for the first time. Crystal structure study of the monomer indicated that though the dihedral angle O3′-C3′-C4′-C5″ in this case would be like in RNA, the sugar conformation would remain like that in DNA. The study of the effect of this backbone configuration in DNA with respect to its binding to cDNA and RNA is reported in this

  摘要首次报道了含有3'→5''键的C4'-epi-DNA的合成。单体的晶体结构研究表明，尽管在这种情况下二面角O3'-C3'-C4'-C5''与RNA相似，但糖构象仍与DNA相似。本说明中报道了在DNA中这种主链构型对其与cDNA和RNA结合的影响的研究。图形概要
• Synthesis and evaluation of oligodeoxynucleotides containing 4′-C-substituted thymidines
  作者：Guangyi Wang、Wilfried E. Seifert

  DOI：10.1016/0040-4039(96)01432-3

  日期：1996.9

  4′-C-Hydroxymethylthymidine was converted to 4′-C-methoxymethylthymidine and 4′-C-aminomethylthymidine, which were incorporated into oligodeoxynucleotides by phosphoramidite chemistry. The modified oligonucleotides exhibit excellent hybridization and significant improvement in stability to snake venom phosphodiesterase.

  将4'- C-羟基甲基胸苷转化为4'- C-甲氧基甲基胸苷和4'- C-氨基甲基胸苷，通过亚磷酰胺化学将其掺入寡脱氧核苷酸中。修饰的寡核苷酸表现出优异的杂交性，并且对蛇毒磷酸二酯酶的稳定性显着提高。