(5S,6R)-6-(tert-butyldiphenylsiloxy)-5-methyl-1-heptene | 175613-29-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (5S,6R)-6-(tert-butyldiphenylsiloxy)-5-methyl-1-heptene
• 英文别名: tert-butyl-[(2R,3S)-3-methylhept-6-en-2-yl]oxy-diphenylsilane
• CAS: 175613-29-3
• 化学式: C₂₄H₃₄OSi
• 分子量: 366.619
• InChiKey: SHNASWIBJLANOT-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5S,6R)-6-(tert-butyldiphenylsiloxy)-5-methyl-1-heptene 在 正丁基锂 、 三丁基膦 、 三氟甲磺酸 、 三氟化硼乙醚 、 potassium tert-butylate 、 臭氧 、 (+)-B-methoxydiisocamphenylborane 作用下， 以 乙醚 为溶剂， 反应 5.91h， 生成 (2S,3S,6S,7R)-7-[tert-butyl(diphenyl)silyl]oxy-3-[(4-methoxyphenyl)methoxy]-2,6-dimethyloctanal
  参考文献：
  名称：

  Synthesis of the C1−C21 Fragment of the Serine/Threonine Phosphatase Inhibitor Tautomycin

  摘要：

  Compound 40 containing the C-1-C-21 region of tautomycin has been synthesized. The two halves (4 and 5) of this spirocyclic section were each constructed using Matteson's chloromethylene insertion reaction. Cr/Ni-mediated coupling of compounds 4 and 5 resulted in a structure containing the C-1-C-21 section of tautomycin. Oxidation of the resultant allylic alcohol to the ketone and removal of the alpha,beta unsaturation yielded compound 39. Treatment with DDQ removed both PMB protecting groups and allowed the spirocyclic ketal to form producing compound 40, ready for further extension to the natural product tautomycin.

  DOI：

  10.1021/jo952083l
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 (5S,6R)-6-(hydroxy)-5-methyl-1-heptene 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以71%的产率得到(5S,6R)-6-(tert-butyldiphenylsiloxy)-5-methyl-1-heptene
  参考文献：
  名称：

  Synthesis of the C1−C21 Fragment of the Serine/Threonine Phosphatase Inhibitor Tautomycin

  摘要：

  Compound 40 containing the C-1-C-21 region of tautomycin has been synthesized. The two halves (4 and 5) of this spirocyclic section were each constructed using Matteson's chloromethylene insertion reaction. Cr/Ni-mediated coupling of compounds 4 and 5 resulted in a structure containing the C-1-C-21 section of tautomycin. Oxidation of the resultant allylic alcohol to the ketone and removal of the alpha,beta unsaturation yielded compound 39. Treatment with DDQ removed both PMB protecting groups and allowed the spirocyclic ketal to form producing compound 40, ready for further extension to the natural product tautomycin.

  DOI：

  10.1021/jo952083l

文献信息

• Synthesis of the C1−C21 Fragment of the Serine/Threonine Phosphatase Inhibitor Tautomycin
  作者：Karl W. Maurer、Robert W. Armstrong

  DOI：10.1021/jo952083l

  日期：1996.1.1

  Compound 40 containing the C-1-C-21 region of tautomycin has been synthesized. The two halves (4 and 5) of this spirocyclic section were each constructed using Matteson's chloromethylene insertion reaction. Cr/Ni-mediated coupling of compounds 4 and 5 resulted in a structure containing the C-1-C-21 section of tautomycin. Oxidation of the resultant allylic alcohol to the ketone and removal of the alpha,beta unsaturation yielded compound 39. Treatment with DDQ removed both PMB protecting groups and allowed the spirocyclic ketal to form producing compound 40, ready for further extension to the natural product tautomycin.