4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,3S)-3-acetyl-5,8-dioxo-3,4,5,8-tetrahydro-1H-isochromen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester | 151767-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,3S)-3-acetyl-5,8-dioxo-3,4,5,8-tetrahydro-1H-isochromen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester
• CAS: 151767-44-1
• 化学式: C₂₆H₂₃F₃N₂O₁₁
• 分子量: 596.471
• InChiKey: OIZYXLFMSAYCKT-VODHSZNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  177.44
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  高邻苯二甲酸酐 、 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,3S)-3-acetyl-5,8-dioxo-3,4,5,8-tetrahydro-1H-isochromen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到[(2S,3S,4S,6S)-6-[[(1R,3S)-3-acetyl-6-hydroxy-5,12-dioxo-3,4-dihydro-1H-naphtho[2,3-g]isochromen-1-yl]oxy]-2-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] 4-nitrobenzoate
  参考文献：
  名称：

  DDQ-Induced, Anomeric Specific, and Diastereoselective Benzylic Glycosidation: A Novel Approach to Heterocyclic Anthracycline Antibiotics

  摘要：

  A novel and efficient method for the oxidative glycosidation at the heterosubstituted benzylic positions with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) is described. The reaction is stereospecific with 3-substituted isochromans and isothiochroman, as well as diastereoselective with non-3-substituted isochromans. The glycosidation with a mixture of alpha- and beta-anomeric free sugars gives alpha-glycosides with absolute stereochemical control on the anomeric center. The synthetic utility of this novel methodology is demonstrated by a short, efficient, and stereoselective total synthesis of heteroanthracycline antitumor reagents.

  DOI：

  10.1021/jo00096a032
• 作为产物：
  描述：

  [(2S,3S,4S,6S)-6-[[(1R,3S)-3-acetyl-5,8-dimethoxy-3,4-dihydro-1H-isochromen-1-yl]oxy]-2-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] 4-nitrobenzoate 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以99%的产率得到4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,3S)-3-acetyl-5,8-dioxo-3,4,5,8-tetrahydro-1H-isochromen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  DDQ-Induced, Anomeric Specific, and Diastereoselective Benzylic Glycosidation: A Novel Approach to Heterocyclic Anthracycline Antibiotics

  摘要：

  A novel and efficient method for the oxidative glycosidation at the heterosubstituted benzylic positions with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) is described. The reaction is stereospecific with 3-substituted isochromans and isothiochroman, as well as diastereoselective with non-3-substituted isochromans. The glycosidation with a mixture of alpha- and beta-anomeric free sugars gives alpha-glycosides with absolute stereochemical control on the anomeric center. The synthetic utility of this novel methodology is demonstrated by a short, efficient, and stereoselective total synthesis of heteroanthracycline antitumor reagents.

  DOI：

  10.1021/jo00096a032