(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 | 1043512-63-5

• 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-(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
• CAS: 1043512-63-5
• 化学式: C₃₁H₄₃N₃O₁₀Si
• 分子量: 645.782
• InChiKey: XROHFIUQCYDBSW-IHDDDBKGSA-N

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-((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 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以85%的产率得到benzyl (1S,2S)-2-(tert-butyldimethylsilyloxy)-1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)but-3-enylcarbamate
  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-((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