7-O-(2',3',4',6'-tetra-O-benzoyl-α-L-rhamnopyranosyl)-4-deoxy-ε-rhodomycinone | 1303970-41-3

• 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: 7-O-(2',3',4',6'-tetra-O-benzoyl-α-L-rhamnopyranosyl)-4-deoxy-ε-rhodomycinone
• 英文别名: methyl (1R,2R,4S)-2-ethyl-2,5,12-trihydroxy-6,11-dioxo-4-[(2R,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxy-3,4-dihydro-1H-tetracene-1-carboxylate
• CAS: 1303970-41-3
• 化学式: C₄₉H₄₂O₁₅
• 分子量: 870.863
• InChiKey: VAMVYNQVZMBXRP-BUTGCUOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  64
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  219
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  7-O-(2',3',4',6'-tetra-O-benzoyl-α-L-rhamnopyranosyl)-4-deoxy-ε-rhodomycinone 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以30 mg的产率得到7-O-(L-rhamnopyranosyl)-4-deoxy-ε-rhodomycinone
  参考文献：
  名称：

  Stereo- and regioselective glycosylation of 4-deoxy-ε-rhodomycinone

  摘要：

  A method for the glycosylation of anthracyclines featuring benzoylated imidate donors has been developed and utilized in the synthesis of glycosylated 4-deoxy-epsilon-rhodomycinone derivatives. Due to its high efficiency, regioselectivity, stereoselectivity, and operational simplicity, the method should prove valuable to researchers working with glycosylation of tetracyclic compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.01.028
• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 methyl (1R,2R,4S)-2-ethyl-2,4,5,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate 、 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 以 二氯甲烷 为溶剂， 反应 0.17h， 以68 mg的产率得到7-O-(2',3',4',6'-tetra-O-benzoyl-α-L-rhamnopyranosyl)-4-deoxy-ε-rhodomycinone
  参考文献：
  名称：

  Stereo- and regioselective glycosylation of 4-deoxy-ε-rhodomycinone

  摘要：

  A method for the glycosylation of anthracyclines featuring benzoylated imidate donors has been developed and utilized in the synthesis of glycosylated 4-deoxy-epsilon-rhodomycinone derivatives. Due to its high efficiency, regioselectivity, stereoselectivity, and operational simplicity, the method should prove valuable to researchers working with glycosylation of tetracyclic compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.01.028

文献信息

• Stereo- and regioselective glycosylation of 4-deoxy-ε-rhodomycinone
  作者：Filip S. Ekholm、Lucas Lagerquist、Reko Leino

  DOI：10.1016/j.carres.2011.01.028

  日期：2011.5

  A method for the glycosylation of anthracyclines featuring benzoylated imidate donors has been developed and utilized in the synthesis of glycosylated 4-deoxy-epsilon-rhodomycinone derivatives. Due to its high efficiency, regioselectivity, stereoselectivity, and operational simplicity, the method should prove valuable to researchers working with glycosylation of tetracyclic compounds. (C) 2011 Elsevier Ltd. All rights reserved.