1,2-di-O-acetyl-3-deoxy-3-[(ethoxycarbonyl)methyl]-5-O-methanesulfonyl-D-ribofuranose | 279248-82-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1,2-di-O-acetyl-3-deoxy-3-[(ethoxycarbonyl)methyl]-5-O-methanesulfonyl-D-ribofuranose
• 英文别名: ethyl 2-[(2S,3R,4R)-4,5-diacetyloxy-2-(methylsulfonyloxymethyl)oxolan-3-yl]acetate
• CAS: 279248-82-7
• 化学式: C₁₄H₂₂O₁₀S
• 分子量: 382.389
• InChiKey: CPKQFFIGFBUOME-KRFDCYKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2-di-O-acetyl-3-deoxy-3-[(ethoxycarbonyl)methyl]-5-O-methanesulfonyl-D-ribofuranose 在 硫酸氢铵 、 sodium hydroxide 、 六甲基二硅氮烷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3'-(carboxymethyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrilyl)-5-methyluridine 2',3'-lactone
  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
• 作为产物：
  描述：

  乙酸酐 、 3-deoxy-3-[(ethoxycarbonyl)methyl]-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-ribofuranose 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 以70%的产率得到1,2-di-O-acetyl-3-deoxy-3-[(ethoxycarbonyl)methyl]-5-O-methanesulfonyl-D-ribofuranose
  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