(2R,3R,4R,5R)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((R,E)-10,10,11,11-tetramethyl-3-oxo-1-phenyl-2,9-dioxa-4-aza-10-siladodec-6-en-5-yl)tetrahydrofuran-3,4-diyl diethanoate | 1043512-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4R,5R)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((R,E)-10,10,11,11-tetramethyl-3-oxo-1-phenyl-2,9-dioxa-4-aza-10-siladodec-6-en-5-yl)tetrahydrofuran-3,4-diyl diethanoate
• 英文别名: [(2R,3R,4R,5R)-4-acetyloxy-2-[(E,1R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(phenylmethoxycarbonylamino)but-2-enyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 1043512-52-2
• 化学式: C₃₁H₄₃N₃O₁₀Si
• 分子量: 645.782
• InChiKey: VRMYIIVQRHLQLO-PYPLQAIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((R,E)-10,10,11,11-tetramethyl-3-oxo-1-phenyl-2,9-dioxa-4-aza-10-siladodec-6-en-5-yl)tetrahydrofuran-3,4-diyl diethanoate 在 碳酸氢钠 、 间氯过氧苯甲酸 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 1.5h， 以0.855 g的产率得到(2R,3R,4R,5R)-2-((R)-benzyloxycarbonylamino)((2R,3R)-3-(hydroxymethyl)oxiran-2-yl)methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate
  参考文献：
  名称：

  合成霉素的研究：胸腺嘧啶核糖核苷衍生物的立体选择性路线。

  摘要：

  The ezomycins are Streptomyces-derived antifungal natural products, belonging to the complex peptidyl nucleoside family of antibiotics. Employing D-serine as a chiral platform, we report herein a novel synthetic route to the bicyclic octosyl nucleoside core of the ezomycins. A key step in the sequence involved a stereoselective 6-exo-trig oxymercuration-oxidation of a strategic delta-hydroxy alkene derivative, toward construction of the trans-fused furopyran ring system as present in the target products. In contrast to the known carbohydrate-based synthetic routes to the above furopyranyl fragment, the present amino acid chiral template approach is expected to offer a more flexible pathway toward potential SAR-targeted structural/stereochemical modifications of this central bicyclic nucleoside component of the ezomycins.

  DOI：

  10.1021/jo801050r
• 作为产物：
  描述：

  、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到(2R,3R,4R,5R)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((R,E)-10,10,11,11-tetramethyl-3-oxo-1-phenyl-2,9-dioxa-4-aza-10-siladodec-6-en-5-yl)tetrahydrofuran-3,4-diyl diethanoate
  参考文献：
  名称：

  合成霉素的研究：胸腺嘧啶核糖核苷衍生物的立体选择性路线。

  摘要：

  The ezomycins are Streptomyces-derived antifungal natural products, belonging to the complex peptidyl nucleoside family of antibiotics. Employing D-serine as a chiral platform, we report herein a novel synthetic route to the bicyclic octosyl nucleoside core of the ezomycins. A key step in the sequence involved a stereoselective 6-exo-trig oxymercuration-oxidation of a strategic delta-hydroxy alkene derivative, toward construction of the trans-fused furopyran ring system as present in the target products. In contrast to the known carbohydrate-based synthetic routes to the above furopyranyl fragment, the present amino acid chiral template approach is expected to offer a more flexible pathway toward potential SAR-targeted structural/stereochemical modifications of this central bicyclic nucleoside component of the ezomycins.

  DOI：

  10.1021/jo801050r