5-(((3S,4R,6S,7S)-7-((tert-butyldimethylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,6-dimethyloctyl)thio)-1-phenyl-1H-tetrazole | 1234693-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(((3S,4R,6S,7S)-7-((tert-butyldimethylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,6-dimethyloctyl)thio)-1-phenyl-1H-tetrazole
• CAS: 1234693-79-8
• 化学式: C₃₁H₄₈N₄O₃SSi
• 分子量: 584.899
• InChiKey: MLUHIVPEAKJRTB-VVEDBRRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.81
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  71.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-(((3S,4R,6S,7S)-7-((tert-butyldimethylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,6-dimethyloctyl)thio)-1-phenyl-1H-tetrazole 在 双氧水 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以95%的产率得到tert-butyl-[(2S,3S,5R,6S)-5-[(4-methoxyphenyl)methoxy]-3,6-dimethyl-8-(1-phenyltetrazol-5-yl)sulfonyloctan-2-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Enantioselective Syntheses of the Proposed Structures of Cytotoxic Macrolides Iriomoteolide-1a and -1b

  摘要：

  Enantioselective total syntheses of the proposed structures of macrolide cytotoxic agents iriomoteolide-1a and -1b have been accomplished. The synthesis was carried out in a convergent and stereoselective manner. However, the present work suggests that the reported structures have been assigned incorrectly. The synthesis features Julia-Kocienski olefination, Sharpless asymmetric epoxidation, Brown asymmetric crotylboration, a Sakurai reaction, an aldol reaction, and enzymatic resolution as the key steps.

  DOI：

  10.1021/ol101105v
• 作为产物：
  描述：

  (3S,4R,6S,7S)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,6-dimethyloctan-1-ol 、 1-苯基-5-巯基四氮唑 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到5-(((3S,4R,6S,7S)-7-((tert-butyldimethylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,6-dimethyloctyl)thio)-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  Enantioselective Syntheses of the Proposed Structures of Cytotoxic Macrolides Iriomoteolide-1a and -1b

  摘要：

  Enantioselective total syntheses of the proposed structures of macrolide cytotoxic agents iriomoteolide-1a and -1b have been accomplished. The synthesis was carried out in a convergent and stereoselective manner. However, the present work suggests that the reported structures have been assigned incorrectly. The synthesis features Julia-Kocienski olefination, Sharpless asymmetric epoxidation, Brown asymmetric crotylboration, a Sakurai reaction, an aldol reaction, and enzymatic resolution as the key steps.

  DOI：

  10.1021/ol101105v