(2Z,4E,6R)-7-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2-methylhepta-2,4-dien-1-ol | 1370655-39-2

• 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: (2Z,4E,6R)-7-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2-methylhepta-2,4-dien-1-ol
• CAS: 1370655-39-2
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: WQTKQSQPRVNRMI-ZZLDEVEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z,4E,6R)-7-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2-methylhepta-2,4-dien-1-ol 在 甲醚 、 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.75h， 以99%的产率得到[(2R,3E,5Z)-7-bromo-2-methoxy-6-methylhepta-3,5-dienoxy]-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Stereoselective Synthesis of the C₅–C₁₈ Fragment of Halichomycin

  摘要：

  An efficient and convergent synthesis of the C-5-C-18 fragment of halichomycin is reported. Butanolide fragment 6 was readily prepared stereoselectively from (R)-Roche ester through catalyst control; dienylic bromide domain 7 was synthesized from (S)-serine by substrate control. C-5-C-18 fragment 2 was rapidly assembled through a stereoselective alkylation of the butanolide with the dienylic bromide, followed by functional group transformations.

  DOI：

  10.1021/jo202602n
• 作为产物：
  描述：

  ethyl (E,4R)-5-[tert-butyl(dimethyl)silyl]oxy-4-methoxypent-2-enoate 在 草酰氯 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.25h， 生成 (2Z,4E,6R)-7-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2-methylhepta-2,4-dien-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of the C₅–C₁₈ Fragment of Halichomycin

  摘要：

  An efficient and convergent synthesis of the C-5-C-18 fragment of halichomycin is reported. Butanolide fragment 6 was readily prepared stereoselectively from (R)-Roche ester through catalyst control; dienylic bromide domain 7 was synthesized from (S)-serine by substrate control. C-5-C-18 fragment 2 was rapidly assembled through a stereoselective alkylation of the butanolide with the dienylic bromide, followed by functional group transformations.

  DOI：

  10.1021/jo202602n

文献信息

• Stereoselective Synthesis of the C₅–C₁₈ Fragment of Halichomycin
  作者：Qingjiang Li、Shiyong Mao、Yuxin Cui、Yanxing Jia

  DOI：10.1021/jo202602n

  日期：2012.4.20

  An efficient and convergent synthesis of the C-5-C-18 fragment of halichomycin is reported. Butanolide fragment 6 was readily prepared stereoselectively from (R)-Roche ester through catalyst control; dienylic bromide domain 7 was synthesized from (S)-serine by substrate control. C-5-C-18 fragment 2 was rapidly assembled through a stereoselective alkylation of the butanolide with the dienylic bromide, followed by functional group transformations.