1'-(3',5'-di-O-benzyl-β-L-ribofuranosyl)uracil | 190584-00-0

• 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: 1'-(3',5'-di-O-benzyl-β-L-ribofuranosyl)uracil
• 英文别名: 1-[(2S,3S,4R,5S)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 190584-00-0
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: ATKQQFREKNNJFT-QESAQDPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  乙酸酐 、 1'-(3',5'-di-O-benzyl-β-L-ribofuranosyl)uracil 在 吡啶 作用下， 以91%的产率得到1'-(2'-O-acetyl-3',5'-di-O-benzyl-β-L-ribofuranosyl)uracil
  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：

  1,2-O-isopropylidene-3,5-di-O-benzyl-β-L-arabinofuranose 在 甲酸 、 4 A molecular sieve 、 potassium tert-butylate 、 水 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 33.25h， 生成 1'-(3',5'-di-O-benzyl-β-L-ribofuranosyl)uracil
  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

文献信息

• Syntheses and Coupling Reactions of 1,2-Anhydro-3,5-Di-<i>O</i>-Benzyl-α-L-Ribofuranose and 1,2-Anhydro-5-<i>O</i>-Benzyl-3-<i>O</i>-Methyl-α-L-Ribofuranose
  作者：Jun Ning、Fanzuo Kong

  DOI：10.1080/07328309708006532

  日期：1997.3

  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.