3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-phthalimido-β-D-galactopyranosyl (1->5)-2',3'-di-O-acetyluridine | 631842-19-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-phthalimido-β-D-galactopyranosyl (1->5)-2',3'-di-O-acetyluridine
• CAS: 631842-19-8
• 化学式: C₃₃H₃₅N₃O₁₇
• 分子量: 745.651
• InChiKey: BHXAEQIZZUZMTJ-PEHVREJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.87
• 重原子数：
  53.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  251.43
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-phthalimido-β-D-galactopyranosyl (1->5)-2',3'-di-O-acetyluridine 在 甲胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以83%的产率得到2''-deoxy-2''-amino-β-D-galactopyranosyl (1->5)-uridine
  参考文献：
  名称：

  Synthesis of 2-amino-2-deoxy-β-glycosyl-(1→5)-nucleosides and the interaction with RNA

  摘要：

  1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-galactopyranose reacted with protected nucleosides in the presence of BF3 as promoter at room temperature to give selectively 2-amino-2-deoxy-beta-glycosyl-(1-->5)nucleosides in good yields. CD spectra and thermal melting studies showed that 2-amino-2-deoxy-beta-D-glucopyranosyl-(1-->5)-nucleosides could interact with RNA in solution and 2-deoxy-2-amino-beta-D-galactopyranosyl-(1-->5)-nucleosides (17-19) exhibit higher affinity to RNA than 2-deoxy-2-amino-beta-D-glucopyranosyl-(1-->5)-nucleosides (14-16). It indicated that the majority of interactions are established between the polar group of glycosylnucleosides and the sugar-phosphate backbone of RNA helices and weak stacking interaction is observed. The different configuration of hydroxyl group on the glycosyl moiety may affect the glycosyl-nucleoside binding to RNA by induced fit. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00278-5
• 作为产物：
  描述：

  2-((2R,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3'',4'',6''-tri-O-acetyl-2''-deoxy-2''-phthalimido-β-D-galactopyranosyl (1->5)-2',3'-di-O-acetyluridine
  参考文献：
  名称：

  Synthesis of 2-amino-2-deoxy-β-glycosyl-(1→5)-nucleosides and the interaction with RNA

  摘要：

  1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-galactopyranose reacted with protected nucleosides in the presence of BF3 as promoter at room temperature to give selectively 2-amino-2-deoxy-beta-glycosyl-(1-->5)nucleosides in good yields. CD spectra and thermal melting studies showed that 2-amino-2-deoxy-beta-D-glucopyranosyl-(1-->5)-nucleosides could interact with RNA in solution and 2-deoxy-2-amino-beta-D-galactopyranosyl-(1-->5)-nucleosides (17-19) exhibit higher affinity to RNA than 2-deoxy-2-amino-beta-D-glucopyranosyl-(1-->5)-nucleosides (14-16). It indicated that the majority of interactions are established between the polar group of glycosylnucleosides and the sugar-phosphate backbone of RNA helices and weak stacking interaction is observed. The different configuration of hydroxyl group on the glycosyl moiety may affect the glycosyl-nucleoside binding to RNA by induced fit. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00278-5