5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-<5-(2'-tert-butyldimethylsilyl)-N-(dimethylaminosulfonyl)imidazolyl>-D-ribitol | 214956-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-<5-(2'-tert-butyldimethylsilyl)-N-(dimethylaminosulfonyl)imidazolyl>-D-ribitol
• 英文别名: 2-[tert-butyl(dimethyl)silyl]-5-[[(4S,5R)-5-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-N,N-dimethylimidazole-1-sulfonamide
• CAS: 214956-61-3
• 化学式: C₂₅H₅₁N₃O₇SSi₂
• 分子量: 593.933
• InChiKey: IZYKWZHRYNEOFK-WVVQBRDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  123.35
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-<5-(2'-tert-butyldimethylsilyl)-N-(dimethylaminosulfonyl)imidazolyl>-D-ribitol 在 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 生成 (2R,3S)-5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-<5-(2'-tert-butyldimethylsilyl)-N-(dimethylaminosulfonyl)imidazolyl>-1,4-pentanedione
  参考文献：
  名称：

  Synthesis and Properties of C-Azalyxonucleosides

  摘要：

  1-beta-(4-Imidazoyl)- and 1-beta-(5-uracilyl)-1,4-dideoxy-1,4-imino-L-lyxitols were synthesized stereoselectively via a sequential procedure by the addition of the corresponding metal salts of heterocycles, Swern oxidation, reductive aminocyclization, and deprotection. Their structures were determined based on X-ray crystallography. From the NMR measurements of their N-acyl derivatives, two rotational isomers were observed. Their bioassay is also described.

  DOI：

  10.1021/jo980492m
• 作为产物：
  描述：

  5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 、 lithium salt of 2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-1-<5-(2'-tert-butyldimethylsilyl)-N-(dimethylaminosulfonyl)imidazolyl>-D-ribitol
  参考文献：
  名称：

  Synthesis and Properties of C-Azalyxonucleosides

  摘要：

  1-beta-(4-Imidazoyl)- and 1-beta-(5-uracilyl)-1,4-dideoxy-1,4-imino-L-lyxitols were synthesized stereoselectively via a sequential procedure by the addition of the corresponding metal salts of heterocycles, Swern oxidation, reductive aminocyclization, and deprotection. Their structures were determined based on X-ray crystallography. From the NMR measurements of their N-acyl derivatives, two rotational isomers were observed. Their bioassay is also described.

  DOI：

  10.1021/jo980492m