2',3',5'-tri-O-benzyl-α-D-uridine | 110522-43-5

• 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: 2',3',5'-tri-O-benzyl-α-D-uridine
• 英文别名: 1-[(2S,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 110522-43-5
• 化学式: C₃₀H₃₀N₂O₆
• 分子量: 514.578
• InChiKey: QLUZOOPFTPUYKP-PXTYPYQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,5-Tri-O-benzoyl-D-ribofuranose 在 potassium fluoride 、 silver trifluoromethanesulfonate 、 diphenyltin sulfide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 2',3',5'-tri-O-benzyl-α-D-uridine
  参考文献：
  名称：

  银盐与硫化二苯锡或劳森试剂联用立体选择性合成β-D-核糖核苷

  摘要：

  β-D-核糖核苷是通过使用 [二苯基锡硫化物/银盐] 或 [劳森试剂] 从甲基 2,3,5-三-O-苯甲酰基-β-D-呋喃核糖基碳酸酯和三甲基甲硅烷基化核苷碱基以高产率立体选择性合成/银盐]在温和条件下组合催化剂体系。

  DOI：

  10.1246/bcsj.67.3100

文献信息

• Condensation of 1-Fluorofuranoses and Silylated Nucleobases Catalyzed by Tetrafluorosilane
  作者：Ryoji Noyori、Masahiko Hayashi

  DOI：10.1246/cl.1987.57

  日期：1987.1.5

  The title reaction provides a generally useful tool for nucleoside synthesis. The stereoselectivities are highly influenced by the fluoride substrates, and steric course of the reaction of O-benzylated ribofuranosyl fluoride is solvent dependent.

  标题反应为核苷合成提供了一个普遍有用的工具。立体选择性受氟化物底物的影响很大，并且 O-苄基化呋喃核糖基氟反应的空间过程是溶剂依赖性的。
• The stereocontrolled synthesis of 1,2-cis furanosyl nucleosides via a novel anomeric activation
  作者：S Hanessian

  DOI：10.1016/00404-0399(50)1179l-

  日期：1995.8.14

  The coupling of 2-(2',3',5'-tri-O-benzyl-D-ribofuranosyloxy)-3-methoxypyridine as well as 2-(2',3',5'-tri-O-benzyl-D-ribofuranosyl with silylated pyrimidine bases by activation with trimethylsilyl trifluoromethanesulfonate and silver triflate respectively affords the corresponding 1,2-cis nucleosides with high selectivity.
• Stereoselective synthesis of nucleosides by metallocene-promoted activation of glycosyl fluorides
  作者：Ma Isabel Matheu、Raouf Echarri、Sergio Catillón

  DOI：10.1016/s0040-4039(00)91869-0

  日期：1992.2

  The Cp2MCl2-AgX (M = Hf, Zr; X = ClO4, OTf) mixture is very effective for the promotion of the coupling of glycosyl fluorides and bis(trimethylsilyl)uracil. The stereoselectivity of the reaction depends on the solvent employed. Application to the synthesis of 1-(3,4 -isopropylidene-2-fluoro-2-O-methyl-alpha-D-ribopentopyranosyl)uracil is described.
• NOERI, REDZI;XAYASI, MASAXIKO
  作者：NOERI, REDZI、XAYASI, MASAXIKO

  DOI：——

  日期：——
• Stereoselective Syntheses of<i>β</i>-D-Ribonucleosides Catalyzed by the Combined Use of Silver Salts and Diphenyltin Sulfide or Lawesson’s Reagent
  作者：Naoyuki Shimomura、Takafumi Matsutani、Teruaki Mukaiyama

  DOI：10.1246/bcsj.67.3100

  日期：1994.11

  β-D-Ribonucleosides are stereoselectively synthesized in high yields from methyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl carbonate and trimethylsilylated nucleoside bases by the use of [diphenyltin sulfide/silver salt] or [Lawesson’s reagent/silver salt] combined catalyst system under mild conditions.

  β-D-核糖核苷是通过使用 [二苯基锡硫化物/银盐] 或 [劳森试剂] 从甲基 2,3,5-三-O-苯甲酰基-β-D-呋喃核糖基碳酸酯和三甲基甲硅烷基化核苷碱基以高产率立体选择性合成/银盐]在温和条件下组合催化剂体系。