3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-2'-α-hydroxymethyluridine | 733050-21-0

• 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',5'-di-O-(4-chlorobenzyl)-2'-deoxy-2'-α-hydroxymethyluridine
• 英文别名: 1-[(2R,3R,4S,5R)-4-[(4-chlorophenyl)methoxy]-5-[(4-chlorophenyl)methoxymethyl]-3-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 733050-21-0
• 化学式: C₂₄H₂₄Cl₂N₂O₆
• 分子量: 507.37
• InChiKey: SAPOXZZQHMQZCY-YXPKMTABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-2'-α-hydroxymethyluridine 在 palladium dihydroxide 、 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 氢气 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 79.5h， 生成 4-amino-1-[(2R,3R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-methyloxolan-2-yl]pyrimidin-2-one
  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 硫酸氢铵 、 sodium hydroxide 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-2'-α-hydroxymethyluridine
  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.