3'-O-trimethylacetylthymidine | 330548-54-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-O-trimethylacetylthymidine
• 英文别名: 5'-O-Trimethylacetyl-thymidin；O^3'-(2,2-dimethyl-propionyl)-thymidine
• CAS: 330548-54-4
• 化学式: C₁₅H₂₂N₂O₆
• 分子量: 326.349
• InChiKey: AUURWWRGOPUURM-HBNTYKKESA-N

反应信息

• 作为反应物：
  描述：

  3'-O-trimethylacetylthymidine 在 吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Nucleoside 5′-C-phosphonates: reactivity of the α-hydroxyphosphonate moiety

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.03.008
• 作为产物：
  描述：

  3',5'-O-bis(trimethylacetyl)thymidine 在 甲醇 、 sodium hydroxide 作用下， 反应 1.0h， 生成 3'-O-trimethylacetylthymidine
  参考文献：
  名称：

  A convenient protection for 4-oxopyrimidine moieties in nucleosides by the pivaloyl group

  摘要：

  对蒽酰基团作为胸腺嘧啶和尿嘧啶N3位置的保护的应用进行了研究。胸腺嘧啶的蒽酰化是一种非常快速的反应，在温和条件下进行，具有对糖或胸嘧啶基团的优异区域选择性，取决于使用的胺类。通过在不同实验条件下使用蒽酰氯处理未受保护的胸腺嘧啶，得到了几种蒽酰化胸腺嘧啶衍生物。评估了N3-蒽酰保护基在酸性和碱性条件下的稳定性，并找到了其选择性去除的条件。

  DOI：

  10.1135/cccc2009084