5-((3S,4S,E)-3-(4-methoxybenzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-(triethylsilyloxy)hex-5-enylsulfonyl)-1-phenyl-1H-tetrazole | 1072083-04-5

• 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,4S,E)-3-(4-methoxybenzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-(triethylsilyloxy)hex-5-enylsulfonyl)-1-phenyl-1H-tetrazole
• 英文别名: triethyl-[(E,3S,4S)-4-[(4-methoxyphenyl)methoxy]-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-(1-phenyltetrazol-5-yl)sulfonylhex-1-en-3-yl]oxysilane
• CAS: 1072083-04-5
• 化学式: C₃₃H₄₆N₄O₆SSi
• 分子量: 654.903
• InChiKey: PBEMXXNLLRZHJG-RIKBVYDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,6S)-2-(tert-butyldimethylsilyloxy)-6-methyl-4-methylene-7-((2R,6R)-6-(prop-2-ynyl)-3,6-dihydro-2H-pyran-2-yl)heptanal 、 5-((3S,4S,E)-3-(4-methoxybenzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-(triethylsilyloxy)hex-5-enylsulfonyl)-1-phenyl-1H-tetrazole 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.7h， 以76%的产率得到(5S,9S,10S,E)-12,12-diethyl-9-(4-methoxybenzyloxy)-2,2,3,3-tetramethyl-5-((S)-4-methyl-2-methylene-5-((2R,6R)-6-(prop-2-ynyl)-3,6-dihydro-2H-pyran-2-yl)pentyl)-10-((E)-2-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)vinyl)-4,11-dioxa-3,12-disilatetradec-6-ene
  参考文献：
  名称：

  Total Synthesis of Neolaulimalide and Isolaulimalide

  摘要：

  The first total syntheses of the potential antitumoral leads neolaulimalide (2) and isolaulimalide (3) have been achieved. Key steps in our convergent, fully stereocontrolled route are a Yamaguchi macrolactonization, a Julia-Lythgoe-Kocienski olefination, a Kulinkovich reaction, and a cyclopropyl-allyl rearrangement to install the exo-methylene group. Overall, we synthesized 2 in 21 linear steps (3% yield) and 3 in 24 steps (2% yield).

  DOI：

  10.1021/ol802075v
• 作为产物：
  描述：

  5-((3S,4S,E)-3-(4-methoxybenzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-(triethylsilyloxy)hex-5-enylthio)-1-phenyl-1H-tetrazole 在 ammonium molybdate 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 以61%的产率得到5-((3S,4S,E)-3-(4-methoxybenzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-(triethylsilyloxy)hex-5-enylsulfonyl)-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  Total Synthesis of Neolaulimalide and Isolaulimalide

  摘要：

  The first total syntheses of the potential antitumoral leads neolaulimalide (2) and isolaulimalide (3) have been achieved. Key steps in our convergent, fully stereocontrolled route are a Yamaguchi macrolactonization, a Julia-Lythgoe-Kocienski olefination, a Kulinkovich reaction, and a cyclopropyl-allyl rearrangement to install the exo-methylene group. Overall, we synthesized 2 in 21 linear steps (3% yield) and 3 in 24 steps (2% yield).

  DOI：

  10.1021/ol802075v

文献信息

• Total Synthesis of Neolaulimalide and Isolaulimalide
  作者：Andreas Gollner、Johann Mulzer

  DOI：10.1021/ol802075v

  日期：2008.10.16

  The first total syntheses of the potential antitumoral leads neolaulimalide (2) and isolaulimalide (3) have been achieved. Key steps in our convergent, fully stereocontrolled route are a Yamaguchi macrolactonization, a Julia-Lythgoe-Kocienski olefination, a Kulinkovich reaction, and a cyclopropyl-allyl rearrangement to install the exo-methylene group. Overall, we synthesized 2 in 21 linear steps (3% yield) and 3 in 24 steps (2% yield).