(2S,3R,4S,5S)-4-[(4-methoxyphenyl)methoxy]-3,5-dimethyl-2-[(2R)-1-triethylsilyloxypropan-2-yl]cycloheptan-1-one | 401912-06-9

• 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: (2S,3R,4S,5S)-4-[(4-methoxyphenyl)methoxy]-3,5-dimethyl-2-[(2R)-1-triethylsilyloxypropan-2-yl]cycloheptan-1-one
• CAS: 401912-06-9
• 化学式: C₂₆H₄₄O₄Si
• 分子量: 448.718
• InChiKey: NTRDWOYCOZNOHK-TZEUXNATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S)-4-[(4-methoxyphenyl)methoxy]-3,5-dimethyl-2-[(2R)-1-triethylsilyloxypropan-2-yl]cycloheptan-1-one 在 吡啶 、 2,4,6-三甲基吡啶 、 四丁基氟化铵 、 potassium carbonate 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 prop-2-enyl (4S,5S,6S,7S,8S)-5-[(4-methoxyphenyl)methoxy]-4,6,8-trimethyl-7-triethylsilyloxy-9-trityloxynonanoate
  参考文献：
  名称：

  Oxabicyclo[3.2.1]octenes in Organic Synthesis:  Direct Ring Opening of Oxabicyclo[3.2.1] Ring Systems with Diisobutylaluminum Hydride and a Silyl Ketene AcetalSynthesis of the Chiral C(19)−C(26) and C(27)−C(32) Fragments of Scytophycin C

  摘要：

  GRAPHICSAn efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.

  DOI：

  10.1021/ol010253c
• 作为产物：
  描述：

  无 在 platinum(IV) oxide 2,4,6-三甲基吡啶 、 锂硼氢 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 18-冠醚-6 、 三(三甲基硅基)硅烷 、 saponification reagent 、 氢气 、 sodium hexamethyldisilazane 、 四丁基碘化铵 、 potassium hydride 、 苯甲酸酐 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 (2S,3R,4S,5S)-4-[(4-methoxyphenyl)methoxy]-3,5-dimethyl-2-[(2R)-1-triethylsilyloxypropan-2-yl]cycloheptan-1-one
  参考文献：
  名称：

  Oxabicyclo[3.2.1]octenes in Organic Synthesis:  Direct Ring Opening of Oxabicyclo[3.2.1] Ring Systems with Diisobutylaluminum Hydride and a Silyl Ketene AcetalSynthesis of the Chiral C(19)−C(26) and C(27)−C(32) Fragments of Scytophycin C

  摘要：

  GRAPHICSAn efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.

  DOI：

  10.1021/ol010253c

文献信息

• Oxabicyclo[3.2.1]octenes in Organic Synthesis:  Direct Ring Opening of Oxabicyclo[3.2.1] Ring Systems with Diisobutylaluminum Hydride and a Silyl Ketene AcetalSynthesis of the Chiral C(19)−C(26) and C(27)−C(32) Fragments of Scytophycin C
  作者：Kevin W. Hunt、Paul A. Grieco

  DOI：10.1021/ol010253c

  日期：2002.1.1

  GRAPHICSAn efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.