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 | 1043512-66-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 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
• 英文别名: benzyl N-[(1S,2S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]but-3-enyl]carbamate
• CAS: 1043512-66-8
• 化学式: C₂₇H₃₉N₃O₈Si
• 分子量: 561.707
• InChiKey: AUCQTBPGWAVMBG-OKYBJSPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  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 在 mercury(II) trifluoroacetate 、 sodium tetrahydroborate 、 氧气 作用下， 以 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以52%的产率得到benzyl (2R,3R,3aS,5R,6R,7S,7aR)-6-(tert-butyldimethylsilyloxy)-3-hydroxy-5-(hydroxymethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)hexahydro-2H-furo[3,2-b]pyran-7-ylcarbamate
  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-((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