(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 | 1043512-58-8

• 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: (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
• 英文别名: [(2R,3R,4R,5R)-4-acetyloxy-2-[(R)-[(2R,3R)-3-(hydroxymethyl)oxiran-2-yl]-(phenylmethoxycarbonylamino)methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 1043512-58-8
• 化学式: C₂₅H₂₉N₃O₁₁
• 分子量: 547.519
• InChiKey: KPLXSDGOHDOLQG-QNIPETCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  182
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (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 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.33h， 生成
  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：

  (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