methyl 5-O-benzyl-3-O-methyl-β-L-ribofuranoside | 190584-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-O-benzyl-3-O-methyl-β-L-ribofuranoside
• CAS: 190584-10-2
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: OJGIOUPQFANIGZ-XUXIUFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 5-O-benzyl-3-O-methyl-β-L-ribofuranoside 在 吡啶 作用下， 以98%的产率得到methyl 2-O-acetyl-5-O-benzyl-3-O-methyl-β-L-ribofuranoside
  参考文献：
  名称：

  Syntheses and Coupling Reactions of 1,2-Anhydro-3,5-Di-O-Benzyl-α-L-Ribofuranose and 1,2-Anhydro-5-O-Benzyl-3-O-Methyl-α-L-Ribofuranose

  摘要：

  1,2-Anhydro-3,5-di-O-benzyl-alpha-L-ribofuranose (7) and 1,2-anhydro-5-O-benzyl-3-O-methyl-alpha-L-ribofuranose (20) were synthesized from L-arabinose via the key intermediates 3,5-di-O-benzyl-2-O-tosyl- (5) and 5-O-benzyl-3-O-methyl-2-O-tosyl-L-arabinofuranose (18) respectively. Condensation of the anhydro sugars with silylated uracil in the absence of catalyst gave the corresponding nucleoside derivatives with free 2'-OH in high yield. Selective glycosylation of 1,2-O-isopropylidene-alpha-D-xylofuranose with 7 afforded (1-->5)-beta-linked disaccharide predominantly in a good yield.

  DOI：

  10.1080/07328309708006532
• 作为产物：
  描述：

  5-O-benzyl-3-O-methyl-2-O-tosyl-L-arabinofuranose 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 methyl 5-O-benzyl-3-O-methyl-β-L-ribofuranoside
  参考文献：
  名称：

  Syntheses and Coupling Reactions of 1,2-Anhydro-3,5-Di-O-Benzyl-α-L-Ribofuranose and 1,2-Anhydro-5-O-Benzyl-3-O-Methyl-α-L-Ribofuranose

  摘要：

  1,2-Anhydro-3,5-di-O-benzyl-alpha-L-ribofuranose (7) and 1,2-anhydro-5-O-benzyl-3-O-methyl-alpha-L-ribofuranose (20) were synthesized from L-arabinose via the key intermediates 3,5-di-O-benzyl-2-O-tosyl- (5) and 5-O-benzyl-3-O-methyl-2-O-tosyl-L-arabinofuranose (18) respectively. Condensation of the anhydro sugars with silylated uracil in the absence of catalyst gave the corresponding nucleoside derivatives with free 2'-OH in high yield. Selective glycosylation of 1,2-O-isopropylidene-alpha-D-xylofuranose with 7 afforded (1-->5)-beta-linked disaccharide predominantly in a good yield.

  DOI：

  10.1080/07328309708006532