(2R,3S,5R)-3-(t-butyldimethylsilyloxy)-2-hydroxymethyl-5-(1-methylpyrimidin-2,4-dion-5-ylethynyl)tetrahydrofuran | 1402090-85-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: (2R,3S,5R)-3-(t-butyldimethylsilyloxy)-2-hydroxymethyl-5-(1-methylpyrimidin-2,4-dion-5-ylethynyl)tetrahydrofuran
• CAS: 1402090-85-0
• 化学式: C₁₈H₂₈N₂O₅Si
• 分子量: 380.516
• InChiKey: QKOAQVRWJHJEPM-SOUVJXGZSA-N

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-3-(t-butyldimethylsilyloxy)-2-hydroxymethyl-5-(1-methylpyrimidin-2,4-dion-5-ylethynyl)tetrahydrofuran 在 四氮唑 、 三氯乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Furanose ring conformations in a 1′-alkynyl C-nucleoside and the dinucleotide

  摘要：

  A large-scale synthesis was carried out for alkynyl C-nucleotide oligomers in order to clarify the structural details of the artificial DNA. A liquid-phase synthesis by means of phosphoramidite methodology enabled us to handle similar to 0.1 g of the DNA oligomers possessing a pseudouracil derivative (T*) as a non-natural nucleobase. H-1 NMR measurements in aqueous media were carried out for the oligomers, succeeded in the accurate assignments of the protons accompanying with determination of the coupling constants (J values). These J values revealed that average conformation of the alkynylribose rings in the DNA was substantially biased toward the S-type conformers (T-2(1)/E-1/T-0(1)). X-ray crystal analysis of the non-natural nucleoside also supported the S-type conformation (E-2/T-2(1)) as seen in natural B-DNA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.057
• 作为产物：
  描述：

  (2R,3S,5R)-3-(t-butyldimethylsilyloxy)-2-(4,4'-dimethoxytrityloxymethyl)-5-(1-methylpyrimidin-2,4-dion-5-ylethynyl)tetrahydrofuran 在 三氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以79%的产率得到(2R,3S,5R)-3-(t-butyldimethylsilyloxy)-2-hydroxymethyl-5-(1-methylpyrimidin-2,4-dion-5-ylethynyl)tetrahydrofuran
  参考文献：
  名称：

  Furanose ring conformations in a 1′-alkynyl C-nucleoside and the dinucleotide

  摘要：

  A large-scale synthesis was carried out for alkynyl C-nucleotide oligomers in order to clarify the structural details of the artificial DNA. A liquid-phase synthesis by means of phosphoramidite methodology enabled us to handle similar to 0.1 g of the DNA oligomers possessing a pseudouracil derivative (T*) as a non-natural nucleobase. H-1 NMR measurements in aqueous media were carried out for the oligomers, succeeded in the accurate assignments of the protons accompanying with determination of the coupling constants (J values). These J values revealed that average conformation of the alkynylribose rings in the DNA was substantially biased toward the S-type conformers (T-2(1)/E-1/T-0(1)). X-ray crystal analysis of the non-natural nucleoside also supported the S-type conformation (E-2/T-2(1)) as seen in natural B-DNA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.057