(3S,6S,7R,8S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8-tetramethyl-5-oxo-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-but-3-enyl ester | 209260-41-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,6S,7R,8S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8-tetramethyl-5-oxo-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-but-3-enyl ester
• CAS: 209260-41-3
• 化学式: C₃₄H₅₇NO₆Si
• 分子量: 603.915
• InChiKey: HEDAKKUMGLABDA-GEYSESIMSA-N

物化性质

• 沸点：
  635.330±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.006±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.24
• 重原子数：
  42.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  98.86
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3S,6S,7R,8S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8-tetramethyl-5-oxo-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-but-3-enyl ester 在 Grubbs catalyst first generation 双氧水 、 potassium hydrogencarbonate 、 乙腈 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (3S,7S,10S,11R,12S)-7,11-Dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach

  摘要：

  AbstractFor structure‐activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem‐dimethyl group at position C‐4 (4,4‐ethano‐epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7–9 for the oxazole series (compounds 2, 14–18, 21–26) and building blocks 8, 30, and 31 for the 4,4‐ethano series (compounds 3,39–43, 46–51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)‐(PCy3)2], and d) epoxidation of the macrocycle double bond.

  DOI：

  10.1002/chem.19970031211
• 作为产物：
  描述：

  2-甲基-3-[4-甲基(3,5-噁唑)]-2-丙醛 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 (-)-B-methoxydiisopinocampheylborane 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (3S,6S,7R,8S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8-tetramethyl-5-oxo-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-but-3-enyl ester
  参考文献：
  名称：

  Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach

  摘要：

  AbstractFor structure‐activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem‐dimethyl group at position C‐4 (4,4‐ethano‐epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7–9 for the oxazole series (compounds 2, 14–18, 21–26) and building blocks 8, 30, and 31 for the 4,4‐ethano series (compounds 3,39–43, 46–51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)‐(PCy3)2], and d) epoxidation of the macrocycle double bond.

  DOI：

  10.1002/chem.19970031211