(2R,3R,3aR,5R,6R,7S,7aR)-7-(benzyloxycarbonylamino)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-furo[3,2-b]pyran-3-yl ethanoate | 1043512-76-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (2R,3R,3aR,5R,6R,7S,7aR)-7-(benzyloxycarbonylamino)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-furo[3,2-b]pyran-3-yl ethanoate
• CAS: 1043512-76-0
• 化学式: C₃₅H₅₅N₃O₁₀Si₂
• 分子量: 734.007
• InChiKey: UWGJIQWVEFTAKH-YYYXYWLKSA-N

反应信息

• 作为反应物：
  描述：

  (2R,3R,3aR,5R,6R,7S,7aR)-7-(benzyloxycarbonylamino)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-furo[3,2-b]pyran-3-yl ethanoate 在 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到(2R,3R,3aR,5R,6R,7S,7aR)-7-(benzyloxycarbonylamino)-6-(tert-butyldimethylsilyloxy)-5-(hydroxymethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-furo[3,2-b]pyran-3-yl ethanoate
  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：

  benzyl (2R,3R,3aS,5R,6R,7S,7aR)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-furo[3,2-b]pyran-7-ylcarbamate 、 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 2.0h， 以88%的产率得到(2R,3R,3aR,5R,6R,7S,7aR)-7-(benzyloxycarbonylamino)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-furo[3,2-b]pyran-3-yl ethanoate
  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