4-<2'-deoxy-β-D-ribofuranosyl>-8-ethyl-1-hydroxybenzonaphtho<1,2-b>pyran-6-one | 139277-29-5

• 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: 4-<2'-deoxy-β-D-ribofuranosyl>-8-ethyl-1-hydroxybenzonaphtho<1,2-b>pyran-6-one
• 英文别名: 8-ethyl-1-hydroxy-4-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]naphtho[1,2-c]isochromen-6-one
• CAS: 139277-29-5
• 化学式: C₂₄H₂₂O₆
• 分子量: 406.435
• InChiKey: SOMVAIYFZRKGQU-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid 4-[(2R,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-hydroxymethyl-2,5-dihydro-furan-2-yl]-8-ethyl-6-oxo-6H-dibenzo[c,h]chromen-1-yl ester 在 甲醇 、 四丁基氟化铵 、 sodium methylate 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 4-<2'-deoxy-β-D-ribofuranosyl>-8-ethyl-1-hydroxybenzonaphtho<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

• 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.