5'-O-(tert-butyldimethylsilyl)-3'-C-hydroxymethylthymidine | 170638-71-8

• 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: 5'-O-(tert-butyldimethylsilyl)-3'-C-hydroxymethylthymidine
• 英文别名: 5'-O-(t-butyldimethylsilyl)-3'-C-(hydroxymethyl)thymidine
• CAS: 170638-71-8
• 化学式: C₁₇H₃₀N₂O₆Si
• 分子量: 386.521
• InChiKey: FRQFHARMTQTWDP-PBFPGSCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  113.78
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-3'-C-hydroxymethylthymidine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 5'-O-(t-butyldimethylsilyl)-3'-O-(2-cyanoethoxy(diisopropylaminophosphino))-3'-C-((4,4'-dimethoxytrityl)oxymethyl)thymidine
  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：

  1-[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 吡啶 、 水 、 叔丁醇 为溶剂， 生成 5'-O-(tert-butyldimethylsilyl)-3'-C-hydroxymethylthymidine
  参考文献：
  名称：

  3'-C-Hydroxymethylthymidine: Synthesis and Incorporation into Oligodeoxynucleotide Analogues

  摘要：

  The stereoselective synthesis of 3'-C-hydroxymethylthymidine (5) in five steps from thymidine has been accomplished and this nucleoside has been incorporated into oligodeoxynucleotides (ODNs) in different ways.

  DOI：

  10.1080/15257779508012502