1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-malononitrile)-β-D-pentofuranosyl>thymine | 158774-98-2

• 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: 1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-malononitrile)-β-D-pentofuranosyl>thymine
• CAS: 158774-98-2
• 化学式: C₄₀H₄₅N₅O₈Si
• 分子量: 751.911
• InChiKey: QWGPAQULYWOCAL-NDZWSBILSA-N

反应信息

• 作为反应物：
  描述：

  1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-malononitrile)-β-D-pentofuranosyl>thymine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以47%的产率得到1-<5-O-(4-monomethoxytrityl)-2-(R)-2-hydroxy-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-ketenimine-α-cyano)-β-D-pentofuranosyl>thymine
  参考文献：
  名称：

  New synthesis of 3′--substituted-3′-nitromethyl-ribo-thymidines

  摘要：

  The 3'-exo-nitromethylene-function in ribo-thymidine, as in 3, has been used for the first lime as a general intermediate in the Michael addition reaction to give varieties of 3'-($) under bar C-subsituted nucleosides (12 - 21). The reaction of the conjugate base of acetylacetone with 3 however gave cis-fused furanose[3.2.1]hexopyranose nucleoside 24 as a major product due to the base catalyzed rearrangement of the initially formed Michael adduct 17. Detailed NMR spectroscopic data have been presented in support of the structural integrity of all reaction products.

  DOI：

  10.1016/s0040-4020(01)86711-9
• 作为产物：
  描述：

  1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-C-exo-nitromethylene-β-D-pentofuranosyl>thymine 在 potassium tert-butylate 作用下， 反应 8.0h， 生成 1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-malononitrile)-β-D-pentofuranosyl>thymine
  参考文献：
  名称：

  New synthesis of 3′--substituted-3′-nitromethyl-ribo-thymidines

  摘要：

  The 3'-exo-nitromethylene-function in ribo-thymidine, as in 3, has been used for the first lime as a general intermediate in the Michael addition reaction to give varieties of 3'-($) under bar C-subsituted nucleosides (12 - 21). The reaction of the conjugate base of acetylacetone with 3 however gave cis-fused furanose[3.2.1]hexopyranose nucleoside 24 as a major product due to the base catalyzed rearrangement of the initially formed Michael adduct 17. Detailed NMR spectroscopic data have been presented in support of the structural integrity of all reaction products.

  DOI：

  10.1016/s0040-4020(01)86711-9