(2R,3R,4R,5R)-2-((1R,2S)-1-(benzyloxycarbonylamino)-2-hydroxybut-3-enyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate | 1043512-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R)-2-((1R,2S)-1-(benzyloxycarbonylamino)-2-hydroxybut-3-enyl)-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-[(1R,2S)-2-hydroxy-1-(phenylmethoxycarbonylamino)but-3-enyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 1043512-61-3
• 化学式: C₂₅H₂₉N₃O₁₀
• 分子量: 531.519
• InChiKey: VPLQBIALPNZCSS-CFPLAWGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (2R,3R,4R,5R)-2-((1R,2S)-1-(benzyloxycarbonylamino)-2-hydroxybut-3-enyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diethanoate 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到(2R,3R,4R,5R)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((5S,6S)-8,8,9,9-tetramethyl-3-oxo-1-phenyl-6-vinyl-2,7-dioxa-4-aza-8-siladecan-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
• 作为产物：
  描述：

  在 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 以0.590 g的产率得到(2R,3R,4R,5R)-2-((1R,2S)-1-(benzyloxycarbonylamino)-2-hydroxybut-3-enyl)-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