methyl 3,4,5-tri(acetyloxy)-6-{[(1R,3R)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy}tetrahydro-2H-2-pyrancarboxylate | 709640-16-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: methyl 3,4,5-tri(acetyloxy)-6-{[(1R,3R)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy}tetrahydro-2H-2-pyrancarboxylate
• 英文别名: (7R,9R)-(-)-idarubicinone-7-methyl(tri-O-acetyl ester)-β-D-glucuronide；methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(1R,3R)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxane-2-carboxylate
• CAS: 709640-16-4
• 化学式: C₃₃H₃₂O₁₆
• 分子量: 684.607
• InChiKey: XXDWJPJAYKKGAV-IYSJUMESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  236
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 3,4,5-tri(acetyloxy)-6-{[(1R,3R)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy}tetrahydro-2H-2-pyrancarboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以82%的产率得到6-{[(1R,3R)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy}-3,4,5-trihydroxytetrahydro-2H-pyrancarboxylic acid
  参考文献：
  名称：

  Facile Total Syntheses of Idarubicinone‐7‐β‐D‐glucuronide: Convenient Preparations of AB‐Ring Synthon Using Some Carboxylic Acid Derivatives

  摘要：

  Regiospecific syntheses of idarubicinone coupled with D-glucuronic acid are described. Cyclization of dimethoxybenzene with carboxylic acid derivatives in polyphosphoric acid (PPA) in one step afforded the naphthalenones 7, which were transformed to the (+/-)-idarubicinone 3b by general methods. Esterification of (+/-)-3b with (S)-(+)-O-acetylmandelic acid with subsequent separation and deprotection gave (+)-3b and (-)-3b. Reaction of separated two stereoisomers with acetobromo-alpha-D-glucuronic acid methyl ester respective followed by hydrolysis using lithium hydroxide and amberite cation exchange resin furnished two kinds of idarubicinone-7-beta-D-glucuronide (20 and 21) that are coupled at C-7 position of idarubicinone.

  DOI：

  10.1081/scc-120030758
• 作为产物：
  描述：

  4-demethoxy-7-deoxydaunomycinone 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 zinc dibromide 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 苯 为溶剂， 反应 66.5h， 生成 methyl 3,4,5-tri(acetyloxy)-6-{[(1R,3R)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy}tetrahydro-2H-2-pyrancarboxylate
  参考文献：
  名称：

  Facile Total Syntheses of Idarubicinone‐7‐β‐D‐glucuronide: Convenient Preparations of AB‐Ring Synthon Using Some Carboxylic Acid Derivatives

  摘要：

  Regiospecific syntheses of idarubicinone coupled with D-glucuronic acid are described. Cyclization of dimethoxybenzene with carboxylic acid derivatives in polyphosphoric acid (PPA) in one step afforded the naphthalenones 7, which were transformed to the (+/-)-idarubicinone 3b by general methods. Esterification of (+/-)-3b with (S)-(+)-O-acetylmandelic acid with subsequent separation and deprotection gave (+)-3b and (-)-3b. Reaction of separated two stereoisomers with acetobromo-alpha-D-glucuronic acid methyl ester respective followed by hydrolysis using lithium hydroxide and amberite cation exchange resin furnished two kinds of idarubicinone-7-beta-D-glucuronide (20 and 21) that are coupled at C-7 position of idarubicinone.

  DOI：

  10.1081/scc-120030758