methyl 2-α-acetoxymethyl-2-deoxy-α-D-ribofuranoside | 733050-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-α-acetoxymethyl-2-deoxy-α-D-ribofuranoside
• 英文别名: [(2S,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-methoxyoxolan-3-yl]methyl acetate
• CAS: 733050-28-7
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: ZKPBMLZQFNBWNK-HXFLIBJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 methyl 2-α-acetoxymethyl-2-deoxy-α-D-ribofuranoside 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-α-acetoxymethyl-3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-ribofuranoside 、 methyl 2-α-acetoxymethyl-3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-α-D-ribofuranoside
  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 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 氢气 、 仲丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 methyl 2-α-acetoxymethyl-2-deoxy-α-D-ribofuranoside
  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