3',5'-dideoxy-3'-C-methylenethymidine | 130109-04-5

• 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: 3',5'-dideoxy-3'-C-methylenethymidine
• CAS: 130109-04-5
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: GERLPZGGINHLBN-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.09
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3',5'-dideoxy-3'-C-methylenethymidine 在 吡啶 、 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 叔丁醇 为溶剂， 反应 6.0h， 以13%的产率得到1-(2,5-dideoxy-3'-C-hydroxymethyl-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of Novel 3′-C-(Hydroxymethyl)thymidines and Oligodeoxynucleotide Analogues Containing Compressed 3′-C-Hydroxymethyl-Linked Phosphodiester Backbones

  摘要：

  Lombardo methylenation of the novel 2'-deoxy-3'-ketonucleosides 4 afforded 2',3'-dideoxy-3'-C-methylene nucleosides 5, which were subjected to catalytic dihydroxylation reactions. In the case of 5'-deoxynucleoside 5a, a 1:1 mixture of 3'-C-hydroxymethyl diastereoisomers 6a and 7a was obtained, whereas the 5'-O-silylated nucleoside 5b afforded 3'-C-(hydroxymethyl)thymidine derivative 6b as the only product. Sharpless asymmetric dihydroxylation of 5a proceeded in low yield to give 5a and 7a as a 10:3 mixture. 5'-O-Silylated nucleoside 6b was converted into the phosphoramidite synthon 9, which was applied in automated syntheses of oligodeoxynucleotides containing novel compressed 3'-C-hydroxymethyl-linked phosphodiester backbones.

  DOI：

  10.1080/15257779508009485
• 作为产物：
  描述：

  5'-chloro-5'-deoxythymidine 在 重铬酸吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 3',5'-dideoxy-3'-C-methylenethymidine
  参考文献：
  名称：

  Synthesis of Novel 3′-C-(Hydroxymethyl)thymidines and Oligodeoxynucleotide Analogues Containing Compressed 3′-C-Hydroxymethyl-Linked Phosphodiester Backbones

  摘要：

  Lombardo methylenation of the novel 2'-deoxy-3'-ketonucleosides 4 afforded 2',3'-dideoxy-3'-C-methylene nucleosides 5, which were subjected to catalytic dihydroxylation reactions. In the case of 5'-deoxynucleoside 5a, a 1:1 mixture of 3'-C-hydroxymethyl diastereoisomers 6a and 7a was obtained, whereas the 5'-O-silylated nucleoside 5b afforded 3'-C-(hydroxymethyl)thymidine derivative 6b as the only product. Sharpless asymmetric dihydroxylation of 5a proceeded in low yield to give 5a and 7a as a 10:3 mixture. 5'-O-Silylated nucleoside 6b was converted into the phosphoramidite synthon 9, which was applied in automated syntheses of oligodeoxynucleotides containing novel compressed 3'-C-hydroxymethyl-linked phosphodiester backbones.

  DOI：

  10.1080/15257779508009485