1-acetoxy-8-ethenyl-4-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)benzonaphtho<1,2-b>pyran-6-one | 122745-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-acetoxy-8-ethenyl-4-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)benzonaphtho<1,2-b>pyran-6-one
• 英文别名: [(2R,3R,4S,5S)-3,4-diacetyloxy-5-(1-acetyloxy-8-ethenyl-6-oxonaphtho[1,2-c]isochromen-4-yl)oxolan-2-yl]methyl acetate
• CAS: 122745-00-0
• 化学式: C₃₂H₂₈O₁₁
• 分子量: 588.568
• InChiKey: CHDZEOPCGZDDHG-ZSEZPNIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-acetoxy-8-ethenyl-4-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)benzonaphtho<1,2-b>pyran-6-one 在 甲醇 、 potassium carbonate 作用下， 反应 2.0h， 以87%的产率得到8-ethenyl-1-hydroxy-4-β-D-ribofuranosylbenzonaphtho<1,2-b>pyran-6-one
  参考文献：
  名称：

  8-Ethenyl-1-hydroxy-4-.beta.-D-ribofuranosylbenzo[d]naphtho[1,2-b]pyran-6-one and 8-ethenyl-1-hydroxy-4-(2'-deoxy-.beta.-D-ribofuranosyl)benzo[d]naphtho[1,2-b]pyran-6-one. Synthetic C-glycosides related to the gilvocarcin, ravidomycin, and chrysomycin antibiotics

  摘要：

  Syntheses of 8-ethenyl-1-hydroxy-4-beta-D-ribofuranosylbenzo[d]naphtho[1,2-b]pyran-6-one (1) and 8-ethenyl-1-hydroxy-4-(2'-deoxy-beta-D-ribofuranosyl)benzo[d]naphtho[1,2-b]pyran-6-one (2) have been accomplished. These two compounds are the first synthetic C-glycosides structurally related to the gilvocarcin, ravidomycin, and chrysomycin antibiotic class which possess the aglycon substituents (hydroxyl at C-1 and ethenyl at C-8) considered critical for the photolytic nicking of DNA. Anthracycline C-glycoside 1 was prepared by a route involving Lewis acid-catalyzed C-glycosyl bond formation between the tetracyclic aglycon and 1,2,3,5-tetra-O-acetyl-D-ribose followed by construction of the aglycon 8-ethenyl substituent from the corresponding ethyl group by radical bromination-dehydrobromination. Synthesis of C-glycoside 2 utilized a different, complementary procedure for C-glycosyl bond formation by palladium-mediated coupling of an iodoaglycon derivative with 1,4-anhydro-2-deoxy-3-O-(tert-butyldiphenylsilyl)-D-erythro-pent-1-enitol, a furanoid glycal designed to form only beta-C-glycosyl bonds in this reaction. In the synthesis of 2, the 8-ethenyl substituent of the aglycon was installed prior to C-glycosyl bond formation since, in this case, attempted ethyl group bromination led instead to conversion of the carbohydrate moiety to a furan.

  DOI：

  10.1021/jo00033a034
• 作为产物：
  描述：

  8-ethyl-1-methoxy-6H-benzonaphtho<1,2-b>pyran-6-one 在 四(三苯基膦)钯 吡啶 、 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 18-冠醚-6 、 三溴化硼 、 四氯化锡 、 碳酸氢钠 、 cesium fluoride 作用下， 以 四氯化碳 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 89.67h， 生成 1-acetoxy-8-ethenyl-4-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)benzonaphtho<1,2-b>pyran-6-one
  参考文献：
  名称：

  8-Ethenyl-1-hydroxy-4-.beta.-D-ribofuranosylbenzo[d]naphtho[1,2-b]pyran-6-one and 8-ethenyl-1-hydroxy-4-(2'-deoxy-.beta.-D-ribofuranosyl)benzo[d]naphtho[1,2-b]pyran-6-one. Synthetic C-glycosides related to the gilvocarcin, ravidomycin, and chrysomycin antibiotics

  摘要：

  Syntheses of 8-ethenyl-1-hydroxy-4-beta-D-ribofuranosylbenzo[d]naphtho[1,2-b]pyran-6-one (1) and 8-ethenyl-1-hydroxy-4-(2'-deoxy-beta-D-ribofuranosyl)benzo[d]naphtho[1,2-b]pyran-6-one (2) have been accomplished. These two compounds are the first synthetic C-glycosides structurally related to the gilvocarcin, ravidomycin, and chrysomycin antibiotic class which possess the aglycon substituents (hydroxyl at C-1 and ethenyl at C-8) considered critical for the photolytic nicking of DNA. Anthracycline C-glycoside 1 was prepared by a route involving Lewis acid-catalyzed C-glycosyl bond formation between the tetracyclic aglycon and 1,2,3,5-tetra-O-acetyl-D-ribose followed by construction of the aglycon 8-ethenyl substituent from the corresponding ethyl group by radical bromination-dehydrobromination. Synthesis of C-glycoside 2 utilized a different, complementary procedure for C-glycosyl bond formation by palladium-mediated coupling of an iodoaglycon derivative with 1,4-anhydro-2-deoxy-3-O-(tert-butyldiphenylsilyl)-D-erythro-pent-1-enitol, a furanoid glycal designed to form only beta-C-glycosyl bonds in this reaction. In the synthesis of 2, the 8-ethenyl substituent of the aglycon was installed prior to C-glycosyl bond formation since, in this case, attempted ethyl group bromination led instead to conversion of the carbohydrate moiety to a furan.

  DOI：

  10.1021/jo00033a034

文献信息

• Synthetic 8-vinylbenzo[d]naphtho[1,2-b]pyran-6-one C-glycoside
  作者：Daw Iong Kwok、G. Doyle Daves

  DOI：10.1021/jo00280a010

  日期：1989.9