(2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-hydroxyethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate | 1104733-86-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-hydroxyethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate
• 英文别名: [(2S,3S,4S,5S)-4-acetyloxy-2-[(1S)-2-hydroxy-1-(phenylmethoxycarbonylamino)ethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 1104733-86-9
• 化学式: C₂₃H₂₇N₃O₁₀
• 分子量: 505.481
• InChiKey: DMWLGCSKEWRQMD-JLCRNFDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-hydroxyethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以183 mg的产率得到(2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-(ethanoyloxy)ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate
  参考文献：
  名称：

  De Novo Synthetic Route to a Combinatorial Library of Peptidyl Nucleosides

  摘要：

  A stereoselective synthetic route has been developed for the combinatorial synthesis of a structurally unique class of C-4' side chain modified peptide-linked nucleosides. The synthetic strategy and approach involves initial synthesis of a strategically functionalized amino butenolide template, utilizing L-serine as a chiral starting material. Subsequent transformation of the above lactone to C4' aminoalkyl substituted nucleosides, followed by the peptidic coupling of the C4' side chain amine with various amino acids completed the syntheses of the target peptidyl nucleosides. Employing the above route, and utilizing a combination of easily available nucleobases (4) and amino acids (6) as the two diversity elements, synthesis of a 24-member combinatorial library of the title peptide-linked nucleosides has been accomplished.

  DOI：

  10.1080/15257770801944394
• 作为产物：
  描述：

  (3S,4S,5S)-5-((S)-3-((benzyloxy)carbonyl)-2,2-dimethyloxazolidin-4-yl)tetrahydrofuran-2,3,4-triyl triacetate 、 O,O-二(三甲基甲硅烷基)胸苷 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以82%的产率得到(2S,3S,4S,5S)-2-((S)-1-(benzyloxycarbonylamino)-2-hydroxyethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate
  参考文献：
  名称：

  Trimethylsilyl Trifluoromethanesulfonate (TMSOTf) Assisted Facile Deprotection of N,O-Acetonides

  摘要：

  [GRAPHICS]Employing TMSOTf as an easily available reagent, we have developed a mild and efficient method for the deprotection of both terminal and internal NO-acetonide functionalities. Various regularly used protecting groups and common organic functional moieties were found to be unaffected by the described reaction conditions. In a few representative examples, the present method was also extended to deprotect acetonides obtained from 1,2-, and 1,3-terminal diols. The acetonide deprotection protocol described herein is expected to be a useful addition to the presently available methods for performing the above transformation.

  DOI：

  10.1021/jo7021923