TBDMS(-3)[TfaNH(-6d)]2-deoxy-L-lyxHexf(a)-thymin-1-yl | 177490-92-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: TBDMS(-3)[TfaNH(-6d)]2-deoxy-L-lyxHexf(a)-thymin-1-yl
• 英文别名: N-[(2S)-2-[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-2-hydroxyethyl]-2,2,2-trifluoroacetamide
• CAS: 177490-92-5
• 化学式: C₁₉H₃₀F₃N₃O₆Si
• 分子量: 481.544
• InChiKey: UIHDWIHBFSPNSN-IGQOVBAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  TBDMS(-3)[TfaNH(-6d)]2-deoxy-L-lyxHexf(a)-thymin-1-yl 在 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 吡啶 为溶剂， 生成 N(iPr)2P(OCH2CH2CN)(-3)[DMT(-5)][TfaNH(-6d)]2-deoxy-L-lyxHexf(a)-thymin-1-yl
  参考文献：
  名称：

  5'- C-支链胸苷：合成，立体化学，并纳入寡脱氧核苷酸

  摘要：

  胸苷转化为其5'（小号） -环氧衍生物，其与亲核试剂反应，得到5'（小号） - Ç氨基甲基，5'（小号） - Ç -azidomethyl-，5'（小号） - Ç -氰基甲基，和5'（小号） - c ^甲氧基甲基-胸苷与定义的立体化学。由醛衍生物制备5'- C-烯丙基-和5'- C-硝基甲基胸苷。在NOE实验的帮助下确定了5'- C-支化胸苷的立体化学。将四个5'- C-支化的胸苷掺入寡脱氧核苷酸中。

  DOI：

  10.1016/0040-4039(96)00418-2
• 作为产物：
  描述：

  1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(2R)-oxiran-2-yl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.0h， 生成 TBDMS(-3)[TfaNH(-6d)]2-deoxy-L-lyxHexf(a)-thymin-1-yl
  参考文献：
  名称：

  Synthesis of 5′-C-Branched Thymidines and Conversion to Phosphoramidites

  摘要：

  Thymidine was converted to its 5'-epoxy derivative, which was reacted with nucleophiles to give 5'-C-aminomethyl-, 5'-C-bromomethyl-, 5'-C-cyanomethyl, and 5'-C-methoxymethylthymidine derivatives with defined stereochemistry. 5'-C-ally-, 5'-C-hydroxymethyl-, 5'-C-hydroxypropyl-, and 5'-C-(imidazole-4-acetamido)metbylthymidine derivatives were also prepared. The 5'-C-branched thymidines were converted to the corresponding phosphoramidites.

  DOI：

  10.1080/07328319808004219

文献信息

• 5′-C-branched thymidines: Synthesis, stereochemistry, and incorporation into oligodeoxynucleotides
  作者：Guangyi Wang、Patrick J. Middleton

  DOI：10.1016/0040-4039(96)00418-2

  日期：1996.4

  Thymidine was converted to its 5′(S)-epoxy derivative, which reacted with nucleophiles to give 5′(S)-C-aminomethyl-, 5′(S)-C-azidomethyl-, 5′(S)-C-cyanomethyl-, and 5′(S)-C-methoxymethyl-thymidine with defined stereochemistry. 5′-C-Allyl- and 5′-C-nitromethylthymidines were prepared from an aldehyde derivative. Stereochemistry of 5′-C-branched thymidines was assigned with the help of NOE experiments

  胸苷转化为其5'（小号） -环氧衍生物，其与亲核试剂反应，得到5'（小号） - Ç氨基甲基，5'（小号） - Ç -azidomethyl-，5'（小号） - Ç -氰基甲基，和5'（小号） - c ^甲氧基甲基-胸苷与定义的立体化学。由醛衍生物制备5'- C-烯丙基-和5'- C-硝基甲基胸苷。在NOE实验的帮助下确定了5'- C-支化胸苷的立体化学。将四个5'- C-支化的胸苷掺入寡脱氧核苷酸中。
• Synthesis of 5′-<i>C</i>-Branched Thymidines and Conversion to Phosphoramidites
  作者：Guangyi Wang、Patrick J. Middleton

  DOI：10.1080/07328319808004219

  日期：1998.6

  Thymidine was converted to its 5'-epoxy derivative, which was reacted with nucleophiles to give 5'-C-aminomethyl-, 5'-C-bromomethyl-, 5'-C-cyanomethyl, and 5'-C-methoxymethylthymidine derivatives with defined stereochemistry. 5'-C-ally-, 5'-C-hydroxymethyl-, 5'-C-hydroxypropyl-, and 5'-C-(imidazole-4-acetamido)metbylthymidine derivatives were also prepared. The 5'-C-branched thymidines were converted to the corresponding phosphoramidites.