methyl (1R,2R,4S)-2-ethyl-2,4,5,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate | 91432-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: methyl (1R,2R,4S)-2-ethyl-2,4,5,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
• CAS: 91432-55-2
• 化学式: C₂₂H₂₀O₈
• 分子量: 412.396
• InChiKey: SGMBBKJOUPQRGM-PSIMQFQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (1R,2R,4S)-2-ethyl-2,4,5,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 7-O-(β-D-glucopyranosyl)-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

• METHODS FOR THE SYNTHESIS OF AMRUBICIN
  申请人：Tsubrik Olga

  公开号：US20100274031A1

  公开（公告）日：2010-10-28

  Methods for producing amrubicin and structural analogs thereof. The present invention encompasses synthetic pathways for the production of amrubicin (Formula I) and structural analogs thereof. The synthetic pathways of the present invention preferably employ as a starting material an anthracycline compound having the generic Formula II: Compounds of Formula II may have any combination of the following identities for the indicated moieties: R 1 , R 2 , R 3 , R 4 , and R 8 may be H, OH, or alkoxy; R 5 may be H, alkyl, or alkoxycarbonyl; R 6 may be H or alkyl; R 7 may be OH or alkyl. In certain embodiments, ε-rhodomycinone or daunomycinone may be used as starting materials according to Formula II. The present invention employs a compound of Formula II as part of a semi-synthetic method that combines traditional chemical synthetic steps with biosynthetic steps to produce amrubicin, derivatives thereof, and structural analogs thereof. The methods of the present invention preferably include a glycosylation reaction whereby an algycon of amrubicin or structural analog thereof is glycosylated to produce the final product.
• 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.