2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine | 733050-19-6

• 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: 2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine
• 英文别名: [(2R,3R,4S,5R)-2-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxy-5-(benzoyloxymethyl)oxolan-3-yl]methyl benzoate
• CAS: 733050-19-6
• 化学式: C₃₈H₃₁N₃O₉
• 分子量: 673.679
• InChiKey: YBPJTLUPTVNROM-MXUMWRETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以50%的产率得到2'-deoxy-2'-α-(hydroxymethyl)-N⁴-benzoylcytidine
  参考文献：
  名称：

  Synthesis of the Phosphoramidite Derivatives of 2‘-Deoxy-2‘-C-α-methylcytidine and 2‘-Deoxy-2‘-C-α-hydroxymethylcytidine:  Analogues for Chemical Dissection of RNA's 2‘-Hydroxyl Group

  摘要：

  Oligonucleotides containing 2'-C-alpha-methyl and 2'-C-alpha-hydroxymethyl modifications enable strategies for delineation of the distinctive role fulfilled by the 2'-hydroxyl group in RNA structure and function. Synthetic routes to the phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-methylcytidine (14%, 15 steps) and 2'-deoxy-2'-C-alpha-hydroxymethylcytidine (19%, 10 steps) from methyl 3,5-di-O-(4-chlorobenzyl)-alpha-D-ribofuranoside are developed.

  DOI：

  10.1021/jo0495337
• 作为产物：
  描述：

  methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside 在 palladium on activated charcoal 吡啶 、 硫酸氢铵 、 氨 、 氢气 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 80.0h， 生成 2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine
  参考文献：
  名称：

  Synthesis of the Phosphoramidite Derivatives of 2‘-Deoxy-2‘-C-α-methylcytidine and 2‘-Deoxy-2‘-C-α-hydroxymethylcytidine:  Analogues for Chemical Dissection of RNA's 2‘-Hydroxyl Group

  摘要：

  Oligonucleotides containing 2'-C-alpha-methyl and 2'-C-alpha-hydroxymethyl modifications enable strategies for delineation of the distinctive role fulfilled by the 2'-hydroxyl group in RNA structure and function. Synthetic routes to the phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-methylcytidine (14%, 15 steps) and 2'-deoxy-2'-C-alpha-hydroxymethylcytidine (19%, 10 steps) from methyl 3,5-di-O-(4-chlorobenzyl)-alpha-D-ribofuranoside are developed.

  DOI：

  10.1021/jo0495337

文献信息

• Synthesis of the Phosphoramidite Derivatives of 2‘-Deoxy-2‘-<i>C</i>-α-methylcytidine and 2‘-Deoxy-2‘-<i>C</i>-α-hydroxymethylcytidine:  Analogues for Chemical Dissection of RNA's 2‘-Hydroxyl Group
  作者：Nan-Sheng Li、Joseph A. Piccirilli

  DOI：10.1021/jo0495337

  日期：2004.7.1

  Oligonucleotides containing 2'-C-alpha-methyl and 2'-C-alpha-hydroxymethyl modifications enable strategies for delineation of the distinctive role fulfilled by the 2'-hydroxyl group in RNA structure and function. Synthetic routes to the phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-methylcytidine (14%, 15 steps) and 2'-deoxy-2'-C-alpha-hydroxymethylcytidine (19%, 10 steps) from methyl 3,5-di-O-(4-chlorobenzyl)-alpha-D-ribofuranoside are developed.