(5S,2'R)-3-[2'-(t-butyldimethylsilanyloxy)-hex-6-enyl]-5-methyl-3-phenylsulfanyldihydrofuran-2-one | 909270-36-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (5S,2'R)-3-[2'-(t-butyldimethylsilanyloxy)-hex-6-enyl]-5-methyl-3-phenylsulfanyldihydrofuran-2-one
• 英文别名: (5S)-3-[(2R)-2-[tert-butyl(dimethyl)silyl]oxyhex-5-enyl]-5-methyl-3-phenylsulfanyloxolan-2-one
• CAS: 909270-36-6
• 化学式: C₂₃H₃₆O₃SSi
• 分子量: 420.689
• InChiKey: UUZUJYPQZGZZAZ-HXIJRHRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,2'R)-3-[2'-(t-butyldimethylsilanyloxy)-hex-6-enyl]-5-methyl-3-phenylsulfanyldihydrofuran-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) sodium acetate 、 间氯过氧苯甲酸 、 对甲苯磺酰肼 、 对苯醌 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (S)-3-[(2R,8R,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-8,11-bis-methoxymethoxy-11-((2R,5R,6R)-5-methoxymethoxy-6-tetradecyl-tetrahydro-pyran-2-yl)-undecyl]-5-methyl-5H-furan-2-one
  参考文献：
  名称：

  Convergent Synthesis of Pyragonicin

  摘要：

  This paper describes a second-generation synthesis of an antitumor tetrahydropyran ( THP) acetogenin, pyragonicin. The key step involved an olefin cross-metathesis between the THP segment and the terminal gamma-lactone residue. The coupling reaction in the presence of Grubbs' second-generation catalyst resulted in an unseparable mixture of a desired coupling product and its one-carbon eliminated product while the use of Grubbs' first-generation catalyst afforded the former exclusively. A novel MOM-migrating reaction found in a cyclization reaction is also discussed.

  DOI：

  10.1021/jo060970q
• 作为产物：
  描述：

  1,2-环氧己-5-烯 在 咪唑 、 sodium hexamethyldisilazane 、 溶剂黄146 、 lithium iodide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.08h， 生成 (5S,2'R)-3-[2'-(t-butyldimethylsilanyloxy)-hex-6-enyl]-5-methyl-3-phenylsulfanyldihydrofuran-2-one
  参考文献：
  名称：

  Convergent Synthesis of Pyragonicin

  摘要：

  This paper describes a second-generation synthesis of an antitumor tetrahydropyran ( THP) acetogenin, pyragonicin. The key step involved an olefin cross-metathesis between the THP segment and the terminal gamma-lactone residue. The coupling reaction in the presence of Grubbs' second-generation catalyst resulted in an unseparable mixture of a desired coupling product and its one-carbon eliminated product while the use of Grubbs' first-generation catalyst afforded the former exclusively. A novel MOM-migrating reaction found in a cyclization reaction is also discussed.

  DOI：

  10.1021/jo060970q

文献信息

• Convergent Synthesis of Pyragonicin
  作者：Shunya Takahashi、Yayoi Hongo、Narihito Ogawa、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/jo060970q

  日期：2006.8.1

  This paper describes a second-generation synthesis of an antitumor tetrahydropyran ( THP) acetogenin, pyragonicin. The key step involved an olefin cross-metathesis between the THP segment and the terminal gamma-lactone residue. The coupling reaction in the presence of Grubbs' second-generation catalyst resulted in an unseparable mixture of a desired coupling product and its one-carbon eliminated product while the use of Grubbs' first-generation catalyst afforded the former exclusively. A novel MOM-migrating reaction found in a cyclization reaction is also discussed.