[(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 | 160236-70-4

• 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: [(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
• CAS: 160236-70-4
• 化学式: C₂₈H₂₉F₃N₂O₁₁
• 分子量: 626.54
• InChiKey: CCEOPIROCXBEEB-CPMINGCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  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 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.08h， 生成 [(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：

  2,3,6-Trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxo-hexopyranose 、 methyl(5,8-dimethoxyisochroman-3-yl)ketone 在 4 A molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以50%的产率得到[(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
  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

文献信息

• DDQ-Induced, Anomeric Specific, and Diastereoselective Benzylic Glycosidation: A Novel Approach to Heterocyclic Anthracycline Antibiotics
  作者：Yao-Chang Xu、Elaine Lebeau、Giorgio Attardo、Peter L. Myers、John W. Gillard

  DOI：10.1021/jo00096a032

  日期：1994.8

  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.