(2R,3S,4R,6R)-6-(5,8-Bis-benzyloxy-1-hydroxy-naphthalen-2-yl)-2-methyl-tetrahydro-pyran-3,4-diol | 176040-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S,4R,6R)-6-(5,8-Bis-benzyloxy-1-hydroxy-naphthalen-2-yl)-2-methyl-tetrahydro-pyran-3,4-diol
• 英文别名: (2R,3S,4R,6R)-6-[1-hydroxy-5,8-bis(phenylmethoxy)naphthalen-2-yl]-2-methyloxane-3,4-diol
• CAS: 176040-46-3
• 化学式: C₃₀H₃₀O₆
• 分子量: 486.565
• InChiKey: YJGJOXFPMAKDDC-LZXUZAFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,6R)-6-(5,8-Bis-benzyloxy-1-hydroxy-naphthalen-2-yl)-2-methyl-tetrahydro-pyran-3,4-diol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以78%的产率得到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 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-羟基对萘醌 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 (2R,3S,4R,6R)-6-(5,8-Bis-benzyloxy-1-hydroxy-naphthalen-2-yl)-2-methyl-tetrahydro-pyran-3,4-diol
  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

• 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.