6-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5-hydroxynaphthalene-1,4-dione | 176040-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5-hydroxynaphthalene-1,4-dione
• CAS: 176040-47-4
• 化学式: C₁₆H₁₆O₆
• 分子量: 304.299
• InChiKey: SJXXIFAINIEGKH-KWZFETQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5-hydroxynaphthalene-1,4-dione 在 四氟硼酸-二乙醚络合物 、 potassium fluoride 、 三乙酰氧基硼 、 双氧水 、 氧气 、 potassium hydrogencarbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 42.5h， 生成 urdamycinone B
  参考文献：
  名称：

  Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels–Alder reaction of C-glycosyl juglone

  摘要：

  The total synthesis of C-glycosyl angucycline, urdamycinone B 1, was achieved via C-glycosidation of naphthol 6 and the unprotected o-olivose 7, and Diels-Alder reaction of the unprotected C-glycosyl juglone 9 and the diene 17 as the key steps.

  DOI：

  10.1039/cc9960000225
• 作为产物：
  描述：

  1,5-二羟基萘 在 thallium(III) nitrate trihydrate 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.5h， 生成 6-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Total Synthesis of C-Glycosylangucycline, Urdamycinone B, Using an Unprotected Sugar

  摘要：

  The total synthesis of urdamycinone B (1), a prototypical member of the C-glycosylangucycline antibiotics, was achieved by a novel and effective strategy without any protecting group in the sugar moiety. The unprotected C-glycosyljuglone 6 was effectively synthesized by the aryl C-glycosidation of 1,5-naphthalenediol (16) with the totally unprotected D-olivose (8) and the subsequent regioselective photooxygenation of the resultant C-glycosylnaphthalenediol 17. On the other hand, the diene 7 was prepared from 3-methyl-2-cyclohexen-1-one (9) in a short step via the cross-coupling of the vinyl triflate 20 and vinylbutyltin (21) and the Wittig reaction of the aldehyde 24 and the phosphine 25. Finally, the regioselective Diels-Alder reaction of the unprotected C-glycosyljuglone 6 and the diene 7, followed by the regioselecitive introduction of the ketone function at the C1 position, led to the total synthesis of 1.

  DOI：

  10.1021/jo990648y

文献信息

• Two-step synthesis of C-glycosyl juglones from unprotected sugars: a novel approach to angucycline antibiotics
  作者：Goh Matsuo、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1039/cc9960002173

  日期：——

  The two-steps synthesis of C-glycosyl juglones, versatile synthetic intermediates for angucycline antibiotics, has been developed by the C-glycosidation of naphthalene-1,5-diol with an unprotected sugar and the subsequent regioselective photooxygenation of the resultant C-glycosyl naphthalenediol.

  萘-1,5-二醇与未保护的糖进行C-糖基化，随后对得到的C-糖基萘二醇进行位点选择性光氧化，从而合成出两种环己烯类抗生素的多功能合成中间体——C-糖苷萘二醇，该合成过程分为两步。
• Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels–Alder reaction of C-glycosyl juglone
  作者：Goh Matsuo、Yuko Miki、Masaya Nakata、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1039/cc9960000225

  日期：——

  The total synthesis of C-glycosyl angucycline, urdamycinone B 1, was achieved via C-glycosidation of naphthol 6 and the unprotected o-olivose 7, and Diels-Alder reaction of the unprotected C-glycosyl juglone 9 and the diene 17 as the key steps.
• Total Synthesis of <i>C</i>-Glycosylangucycline, Urdamycinone B, Using an Unprotected Sugar
  作者：Goh Matsuo、Yuko Miki、Masaya Nakata、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1021/jo990648y

  日期：1999.9.1

  The total synthesis of urdamycinone B (1), a prototypical member of the C-glycosylangucycline antibiotics, was achieved by a novel and effective strategy without any protecting group in the sugar moiety. The unprotected C-glycosyljuglone 6 was effectively synthesized by the aryl C-glycosidation of 1,5-naphthalenediol (16) with the totally unprotected D-olivose (8) and the subsequent regioselective photooxygenation of the resultant C-glycosylnaphthalenediol 17. On the other hand, the diene 7 was prepared from 3-methyl-2-cyclohexen-1-one (9) in a short step via the cross-coupling of the vinyl triflate 20 and vinylbutyltin (21) and the Wittig reaction of the aldehyde 24 and the phosphine 25. Finally, the regioselective Diels-Alder reaction of the unprotected C-glycosyljuglone 6 and the diene 7, followed by the regioselecitive introduction of the ketone function at the C1 position, led to the total synthesis of 1.