p-methoxybenzyl 2,3,6-trideoxy-α-L-lyxo-hexopyranoside | 452071-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: p-methoxybenzyl 2,3,6-trideoxy-α-L-lyxo-hexopyranoside
• CAS: 452071-62-4
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: XSCYLICWZCJHDV-LEWSCRJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl 2,3,6-trideoxy-α-L-lyxo-hexopyranoside 在 吡啶 、 ammonium cerium(IV) nitrate 、 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 4 A molecular sieve 作用下， 以 乙醚 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 6.0h， 生成 4-O-(3-N-allyloxycarbonyl-4-O-p-nitrobenzoyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-1-O-p-nitrobenzoyl-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Novel anthracycline oligosaccharides: influence of chemical modifications of the carbohydrate moiety on biological activity

  摘要：

  Several observations highlight the importance of the carbohydrate moiety for the biological activity of antitumoural anthracyclines. Here is reported the synthesis, cytotoxicity and topoisomerase II-mediated DNA cleavage intensity of the new oligosaccharide anthracyclines 1-4 modified in the sugar residue. Evaluation of cytotoxic potency on different cell lines, resulted in quite similar values among the different analogues. On the other hand, topoisomerase II-mediated DNA breaks level was different for the various compounds. and was not related to cytotoxicity, thus supporting previous observations reported for some monosaccharide anthracyclines modified in the carbohydrate portion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00411-4
• 作为产物：
  描述：

  4-甲氧基苄醇 在 Wilkinson's catalyst 氢气 、 sodium methylate 、 四氯化锡 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 p-methoxybenzyl 2,3,6-trideoxy-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Novel anthracycline oligosaccharides: influence of chemical modifications of the carbohydrate moiety on biological activity

  摘要：

  Several observations highlight the importance of the carbohydrate moiety for the biological activity of antitumoural anthracyclines. Here is reported the synthesis, cytotoxicity and topoisomerase II-mediated DNA cleavage intensity of the new oligosaccharide anthracyclines 1-4 modified in the sugar residue. Evaluation of cytotoxic potency on different cell lines, resulted in quite similar values among the different analogues. On the other hand, topoisomerase II-mediated DNA breaks level was different for the various compounds. and was not related to cytotoxicity, thus supporting previous observations reported for some monosaccharide anthracyclines modified in the carbohydrate portion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00411-4

文献信息

• Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A
  作者：Hem Raj Khatri、Hai Nguyen、James K. Dunaway、Jianglong Zhu

  DOI：10.1002/chem.201502113

  日期：2015.9.21

  The first total synthesis of derhodinosylurdamycin A, an angucycline antitumor antibiotic, has been described. The synthesis features a Hauser annulation followed by pinacol coupling to construct the tetracyclic angular aglycon, a Stille coupling of glycal stannane and tetracyclic aryliodide followed by stereoselective reduction to afford the 2‐deoxy β‐C‐arylglycoside, and a late‐stage stereoselective

  已经描述了金刚霉素抗肿瘤抗生素derhodinosylurdamycin A的第一个全合成。合成的特征是豪瑟环合，然后频哪醇偶联，以构建四环角糖苷配基；糖锡烷和四环芳基碘的斯蒂尔偶联，然后进行立体选择性还原，得到2-脱氧β-C-芳基糖苷；以及后期的立体选择性糖基化反应该合成策略应适合于化学合成具有不同2-脱氧糖亚基的derhodinosylurdamycin A类似物的化学合成，以进行结构和活性关系研究。