dimethyl-[1-methyl-3-[(E)-2-phenylsulfanylethenyl]cyclohex-3-en-1-yl]-phenylsilane | 245657-04-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: dimethyl-[1-methyl-3-[(E)-2-phenylsulfanylethenyl]cyclohex-3-en-1-yl]-phenylsilane
• CAS: 245657-04-9
• 化学式: C₂₃H₂₈SSi
• 分子量: 364.627
• InChiKey: YNVCDFABDHWLSI-FBMGVBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dimethyl-[1-methyl-3-[(E)-2-phenylsulfanylethenyl]cyclohex-3-en-1-yl]-phenylsilane 在 四氟硼酸-二乙醚络合物 、 三乙酰氧基硼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 9-((2R,4R,5S,6R)-4,5-Dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-(fluoro-dimethyl-silanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydro-benzo[a]anthracene-7,12-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：

  3-(dimethyl(phenyl)silyl)-3-methylcyclohexanone 在 四(三苯基膦)钯 sodium periodate 、 AD-mix-β 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 16.0h， 生成 dimethyl-[1-methyl-3-[(E)-2-phenylsulfanylethenyl]cyclohex-3-en-1-yl]-phenylsilane
  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.