1,4-Bis-benzyloxy-5-methoxymethoxy-naphthalene | 176040-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-Bis-benzyloxy-5-methoxymethoxy-naphthalene
• CAS: 176040-44-1
• 化学式: C₂₆H₂₄O₄
• 分子量: 400.474
• InChiKey: SIHVFIPBYCAPFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,4-Bis-benzyloxy-5-methoxymethoxy-naphthalene 在 palladium on activated charcoal 四氟硼酸-二乙醚络合物 、 potassium fluoride 、 三乙酰氧基硼 、 三氟甲磺酸三甲基硅酯 、 氢气 、 双氧水 、 氧气 、 potassium hydrogencarbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 47.5h， 生成 (3S)-9-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
  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：

  5-(methoxymethoxy)-1,4-naphthoquinone 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1,4-Bis-benzyloxy-5-methoxymethoxy-naphthalene
  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

文献信息

• 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.