2',5'-di-O-acetyl-3'-deoxy-3'-[(methoxycarbonyl)methyl]-5-methyluridine

• 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',5'-di-O-acetyl-3'-deoxy-3'-[(methoxycarbonyl)methyl]-5-methyluridine
• 英文别名: methyl 2-[(2S,3R,4R,5R)-4-acetoxy-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-3-yl]acetate；methyl 2-[(2S,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]acetate
• 化学式: C₁₇H₂₂N₂O₉
• 分子量: 398.37
• InChiKey: PCQHTOFBKOOUGO-ZNEHSRBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,2-di-O-acetyl-3-deoxy-3-[(methoxycarbonyl)methyl]-5-O-methanesulfonyl-D-ribofuranose 在 硫酸氢铵 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 生成 2',5'-di-O-acetyl-3'-deoxy-3'-[(methoxycarbonyl)methyl]-5-methyluridine
  参考文献：
  名称：

  Glucose-Derived 3‘-(Carboxymethyl)-3‘-deoxyribonucleosides and 2‘,3‘-Lactones as Synthetic Precursors for Amide-Linked Oligonucleotide Analogues¹

  摘要：

  Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2'-O-(tert-butyldimethylsilyl) ethers of 5'-azido-5'-deoxy- or 5'-O-(dimethoxytrityl) derivatives of 3'-(carboxymethyl)-3'-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides.

  DOI：

  10.1021/jo991399g

文献信息

• Glucose-Derived 3‘-(Carboxymethyl)-3‘-deoxyribonucleosides and 2‘,3‘-Lactones as Synthetic Precursors for Amide-Linked Oligonucleotide Analogues¹
  作者：Morris J. Robins、Bogdan Doboszewski、Victor A. Timoshchuk、Matt A. Peterson

  DOI：10.1021/jo991399g

  日期：2000.5.1

  Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2'-O-(tert-butyldimethylsilyl) ethers of 5'-azido-5'-deoxy- or 5'-O-(dimethoxytrityl) derivatives of 3'-(carboxymethyl)-3'-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides.