8-ethyl-1-<(triisopropylsilyl)oxy>benzonaphtho<1,2-b>pyran-6-one | 122744-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 8-ethyl-1-<(triisopropylsilyl)oxy>benzonaphtho<1,2-b>pyran-6-one
• 英文别名: 8-Ethyl-1-tri(propan-2-yl)silyloxynaphtho[1,2-c]isochromen-6-one
• CAS: 122744-96-1
• 化学式: C₂₈H₃₄O₃Si
• 分子量: 446.662
• InChiKey: PBVDCOXOMLJYDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.22
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-ethyl-1-<(triisopropylsilyl)oxy>benzonaphtho<1,2-b>pyran-6-one 在 吡啶 、 18-冠醚-6 、 四氯化锡 、 cesium fluoride 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 36.17h， 生成 1-acetoxy-8-ethyl-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
• 作为产物：
  描述：

  8-ethyl-1-methoxy-6H-benzonaphtho<1,2-b>pyran-6-one 在 咪唑 、 三溴化硼 作用下， 生成 8-ethyl-1-<(triisopropylsilyl)oxy>benzonaphtho<1,2-b>pyran-6-one
  参考文献：
  名称：

  Synthetic 8-vinylbenzo[d]naphtho[1,2-b]pyran-6-one C-glycoside

  摘要：

  DOI：

  10.1021/jo00280a010

文献信息

• KWOK, DAW-IONG;DAVES, G. DOYLE (JR), J. ORG. CHEM., 54,(1989) N9, C. 4496-4497
  作者：KWOK, DAW-IONG、DAVES, G. DOYLE (JR)

  DOI：——

  日期：——
• 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
• 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
  作者：Roger N. Farr、Daw Iong Kwok、G. Doyle Daves

  DOI：10.1021/jo00033a034

  日期：1992.3

  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.