(E)-(6S,7S,10S,12R)-7-(tert-Butyl-dimethyl-silanyloxy)-6,8,10,12-tetramethyl-tetradec-8-enoic acid methyl ester | 306275-09-2

• 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: (E)-(6S,7S,10S,12R)-7-(tert-Butyl-dimethyl-silanyloxy)-6,8,10,12-tetramethyl-tetradec-8-enoic acid methyl ester
• 英文别名: methyl (E,6S,7S,10S,12R)-7-[tert-butyl(dimethyl)silyl]oxy-6,8,10,12-tetramethyltetradec-8-enoate
• CAS: 306275-09-2
• 化学式: C₂₅H₅₀O₃Si
• 分子量: 426.756
• InChiKey: VRADUVLIIJDOQP-NTXRCTLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.76
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(6S,7S,10S,12R)-7-(tert-Butyl-dimethyl-silanyloxy)-6,8,10,12-tetramethyl-tetradec-8-enoic acid methyl ester 在 palladium diacetate 、 三氯溴甲烷 、 四丁基氟化铵 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 4-Hydroxy-5-(4-methoxymethoxy-phenyl)-1-methyl-3-[(2R,5S,6S)-5-methyl-6-((E)-(3S,5R)-1,3,5-trimethyl-hept-1-enyl)-tetrahydro-pyran-2-yl]-1H-pyridin-2-one
  参考文献：
  名称：

  Construction of 4-Hydroxy-2-pyridinones. Total Synthesis of (+)-Sambutoxin

  摘要：

  [GRAPHICS]Total synthesis of (+)-sambutoxin has been achieved, establishing the relative and absolute stereochemistry of the naturally occurring mycotoxin, Efforts feature methodology for enantiocontrolled construction of 1,3-anti dimethyl arrays and a novel Saegusa oxidation to provide a pyridinone methide leading to formation of the central dihydropyran ring.

  DOI：

  10.1021/ol006410+
• 作为产物：
  描述：

  Benzoic acid (E)-(1S,3R,4S,7S,9R)-4-hydroxy-1,3,5,7,9-pentamethyl-2-oxo-undec-5-enyl ester 在 咪唑 、 2,3,5-三甲基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 锂硼氢 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (E)-(6S,7S,10S,12R)-7-(tert-Butyl-dimethyl-silanyloxy)-6,8,10,12-tetramethyl-tetradec-8-enoic acid methyl ester
  参考文献：
  名称：

  Construction of 4-Hydroxy-2-pyridinones. Total Synthesis of (+)-Sambutoxin

  摘要：

  [GRAPHICS]Total synthesis of (+)-sambutoxin has been achieved, establishing the relative and absolute stereochemistry of the naturally occurring mycotoxin, Efforts feature methodology for enantiocontrolled construction of 1,3-anti dimethyl arrays and a novel Saegusa oxidation to provide a pyridinone methide leading to formation of the central dihydropyran ring.

  DOI：

  10.1021/ol006410+

文献信息

• Construction of 4-Hydroxy-2-pyridinones. Total Synthesis of (+)-Sambutoxin
  作者：David R. Williams、Regis A. Turske

  DOI：10.1021/ol006410+

  日期：2000.10.1

  [GRAPHICS]Total synthesis of (+)-sambutoxin has been achieved, establishing the relative and absolute stereochemistry of the naturally occurring mycotoxin, Efforts feature methodology for enantiocontrolled construction of 1,3-anti dimethyl arrays and a novel Saegusa oxidation to provide a pyridinone methide leading to formation of the central dihydropyran ring.