1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzoyl-β-D-ribo-furanosyl)uracil | 685137-23-9

• 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: 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzoyl-β-D-ribo-furanosyl)uracil
• 英文别名: [(2R,3R,4R,5R)-4-acetamidosulfanylcarbonyloxy-3-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 685137-23-9
• 化学式: C₂₆H₂₃N₃O₁₀S
• 分子量: 569.549
• InChiKey: PEACSSYYNNRHFR-ZHHKINOHSA-N

物化性质

• 熔点：
  171-172 °C
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  192
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzoyl-β-D-ribo-furanosyl)uracil 在 氢氧化钾 作用下， 以 水 为溶剂， 以89%的产率得到尿嘧啶核苷
  参考文献：
  名称：

  Highly β-stereoselective nucleosidation from α-d-xylo- and α-d-ribo-furanose 1,2-thiocarbonates

  摘要：

  Cyclic 1,2-thiocarbonates of alpha-D-xylo- and alpha-D-ribo-furanoses were found to be excellent glycosyl donors in mild NIS-mediated nucleophilic substitution reactions, affording beta-nucleosides with complete stereo selectivity and moderate to high yields after treatment with persilylated pyrimidinic bases. The nucleophile is believed to open the thiocarbonate ring at the anomeric position presumably via an S(N)2 mechanism. Participation of the nucleobase silylating agent [N,O-bis(trimethylsilyl)acetamide] in the mechanism of the nucleosidation step was shown, where a large excess of it has been proven to be necessary in order to achieve high yields. Absolute configurations at C-1' were ascertained by chemical correlation synthesizing the corresponding 2,2'-anhydronucleosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.037
• 作为产物：
  描述：

  以 二氯甲烷 、 乙腈 为溶剂， 反应 0.92h， 生成 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzoyl-β-D-ribo-furanosyl)uracil
  参考文献：
  名称：

  Highly β-stereoselective nucleosidation from α-d-xylo- and α-d-ribo-furanose 1,2-thiocarbonates

  摘要：

  Cyclic 1,2-thiocarbonates of alpha-D-xylo- and alpha-D-ribo-furanoses were found to be excellent glycosyl donors in mild NIS-mediated nucleophilic substitution reactions, affording beta-nucleosides with complete stereo selectivity and moderate to high yields after treatment with persilylated pyrimidinic bases. The nucleophile is believed to open the thiocarbonate ring at the anomeric position presumably via an S(N)2 mechanism. Participation of the nucleobase silylating agent [N,O-bis(trimethylsilyl)acetamide] in the mechanism of the nucleosidation step was shown, where a large excess of it has been proven to be necessary in order to achieve high yields. Absolute configurations at C-1' were ascertained by chemical correlation synthesizing the corresponding 2,2'-anhydronucleosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.037

文献信息

• Highly β-stereoselective nucleosidation from α-d-xylo- and α-d-ribo-furanose 1,2-thiocarbonates
  作者：Rafael Robles、Concepción Rodrı́guez、Luis Álvarez de Cienfuegos、Antonio J. Mota

  DOI：10.1016/j.tetasy.2003.12.037

  日期：2004.3

  Cyclic 1,2-thiocarbonates of alpha-D-xylo- and alpha-D-ribo-furanoses were found to be excellent glycosyl donors in mild NIS-mediated nucleophilic substitution reactions, affording beta-nucleosides with complete stereo selectivity and moderate to high yields after treatment with persilylated pyrimidinic bases. The nucleophile is believed to open the thiocarbonate ring at the anomeric position presumably via an S(N)2 mechanism. Participation of the nucleobase silylating agent [N,O-bis(trimethylsilyl)acetamide] in the mechanism of the nucleosidation step was shown, where a large excess of it has been proven to be necessary in order to achieve high yields. Absolute configurations at C-1' were ascertained by chemical correlation synthesizing the corresponding 2,2'-anhydronucleosides. (C) 2004 Elsevier Ltd. All rights reserved.