[(2R,3R,4R,6S)-6-[(2R,3R,4S,5S)-6-fluoro-2-methyl-4-phenylmethoxy-5-phenylselanyloxan-3-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-2-methoxy-6-methyl-4-phenylmethoxybenzoate | 306747-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,6S)-6-[(2R,3R,4S,5S)-6-fluoro-2-methyl-4-phenylmethoxy-5-phenylselanyloxan-3-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-2-methoxy-6-methyl-4-phenylmethoxybenzoate
• CAS: 306747-69-3
• 化学式: C₄₉H₅₆Cl₂FNO₁₃Se
• 分子量: 1035.85
• InChiKey: OVYVXIIHDRMUDU-BIKRJOIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.62
• 重原子数：
  67
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  155
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  、 [(2R,3R,4R,6S)-6-[(2R,3R,4S,5S)-6-fluoro-2-methyl-4-phenylmethoxy-5-phenylselanyloxan-3-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-2-methoxy-6-methyl-4-phenylmethoxybenzoate 在 4 A molecular sieve 、 tin(ll) chloride 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以62%的产率得到
  参考文献：
  名称：

  Total Synthesis of Everninomicin 13,384-1—Part 3: Synthesis of the DE Fragment and Completion of the Total Synthesis

  摘要：

  The stereoselective construction of the DE fragment (2) of everninomicin 13,384-1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A1B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.

  DOI：

  10.1002/1521-3765(20000901)6:17<3149::aid-chem3149>3.0.co;2-l
• 作为产物：
  描述：

  [(2R,3S,4R,6S)-6-[(2R,3R,4S,5R,6S)-5-acetyloxy-2-methyl-4-phenylmethoxy-6-phenylselanyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl] 3,5-dichloro-2-methoxy-6-methyl-4-phenylmethoxybenzoate 在 sodium hydroxide 、 4 A molecular sieve 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 tin(ll) chloride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 [(2R,3R,4R,6S)-6-[(2R,3R,4S,5S)-6-fluoro-2-methyl-4-phenylmethoxy-5-phenylselanyloxan-3-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3,5-dichloro-2-methoxy-6-methyl-4-phenylmethoxybenzoate
  参考文献：
  名称：

  Everninomicin的总合成13,384-1--第1部分：A1B（A）C片段的逆合成分析和合成。

  摘要：

  在这四篇文章的系列文章的第一篇中，我们介绍了抗鸟药有效的抗药性强大的抗生素everninomicin 13,384-1（1），作为总合成的目标，并讨论了其逆合成分析。根据合成所需的三个定义的片段（2：A1B（A）C片段； 4：DE片段； 5：FGHA2片段），我们在此处描述了A1B（A）C嵌段的两种方法。第一种策略依靠烯烃复分解反应来构建环B和C的通用中间体，但面临最终的保护基问题。第二种成功的方法涉及1，2-苯磺基迁移和连接环B和C的硫定向糖苷化步骤，以及安装空间位阻芳基酯部分（环A1）的酰基氟中间体。

  DOI：

  10.1002/1521-3765(20000901)6:17<3095::aid-chem3095>3.0.co;2-4

文献信息

• Total Synthesis of Everninomicin 13,384-1—Part 1: Retrosynthetic Analysis and Synthesis of the A1B(A)C Fragment
  作者：K. C. Nicolaou、Rosa Maria Rodríguez、Helen J. Mitchell、Hideo Suzuki、Konstantina C. Fylaktakidou、Olivier Baudoin、Floris L. van Delft

  DOI：10.1002/1521-3765(20000901)6:17<3095::aid-chem3095>3.0.co;2-4

  日期：2000.9.1

  intermediate for rings B and C, but was faced with final protecting group problems. The second, and successful approach, involved a 1,2-phenylsulfeno migration and a sulfur directed glycosidation procedure to link rings B and C, as well as an acyl fluoride intermediate to install the sterically hindered aryl ester moiety (ring A1). The final stages of the synthesis of the required 2-phenylseleno glycosyl fluoride

  在这四篇文章的系列文章的第一篇中，我们介绍了抗鸟药有效的抗药性强大的抗生素everninomicin 13,384-1（1），作为总合成的目标，并讨论了其逆合成分析。根据合成所需的三个定义的片段（2：A1B（A）C片段； 4：DE片段； 5：FGHA2片段），我们在此处描述了A1B（A）C嵌段的两种方法。第一种策略依靠烯烃复分解反应来构建环B和C的通用中间体，但面临最终的保护基问题。第二种成功的方法涉及1，2-苯磺基迁移和连接环B和C的硫定向糖苷化步骤，以及安装空间位阻芳基酯部分（环A1）的酰基氟中间体。
• Total Synthesis of Everninomicin 13,384-1—Part 3: Synthesis of the DE Fragment and Completion of the Total Synthesis
  作者：K. C. Nicolaou、Helen J. Mitchell、Rosa Maria Rodríguez、Konstantina C. Fylaktakidou、Hideo Suzuki、Scott R. Conley

  DOI：10.1002/1521-3765(20000901)6:17<3149::aid-chem3149>3.0.co;2-l

  日期：2000.9.1

  The stereoselective construction of the DE fragment (2) of everninomicin 13,384-1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A1B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.