N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide | 166593-56-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide
• CAS: 166593-56-2
• 化学式: C₂₅H₃₂N₆O₈
• 分子量: 544.564
• InChiKey: WCMUCXUHTQHSFK-AGFSROSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  183.99
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide 在 吡啶 作用下， 以88%的产率得到N-{9-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-propoxy-tetrahydro-furan-2-yl}-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide
  参考文献：
  名称：

  Efficient synthesis of 2′-O-alkyl ribonucleosides using trichloroacetimidate d-ribofuranosides as ribosyl donors

  摘要：

  Trichloroacetimidate-2-O-alkyl-3, 5-O-TIPS-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. This method has been applied to the synthesis of 2'-O-alkyl ribonucleosides further transformed to building blocks ready for oligo(2'-O-alkyl)ribonucleotide construction.

  DOI：

  10.1016/s0040-4039(00)75987-9
• 作为产物：
  描述：

  2,2,2-Trichloro-acetimidic acid (2S,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-propoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl ester 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide
  参考文献：
  名称：

  Efficient synthesis of 2′-O-alkyl ribonucleosides using trichloroacetimidate d-ribofuranosides as ribosyl donors

  摘要：

  Trichloroacetimidate-2-O-alkyl-3, 5-O-TIPS-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. This method has been applied to the synthesis of 2'-O-alkyl ribonucleosides further transformed to building blocks ready for oligo(2'-O-alkyl)ribonucleotide construction.

  DOI：

  10.1016/s0040-4039(00)75987-9