(2'R,5S,8'R,11'R,12'R,15'R,16'R)-3-[2'-(tert-butyldimethylsilanyloxy)-8',11',15'-(trimethoxymethoxy)-12',16'-oxidotriacontanyl]-5-methyl-3-phenylsulfanyldihydrofuran-2-one | 909270-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'R,5S,8'R,11'R,12'R,15'R,16'R)-3-[2'-(tert-butyldimethylsilanyloxy)-8',11',15'-(trimethoxymethoxy)-12',16'-oxidotriacontanyl]-5-methyl-3-phenylsulfanyldihydrofuran-2-one
• 英文别名: (5S)-3-[(2R,8R,11R)-2-[tert-butyl(dimethyl)silyl]oxy-8,11-bis(methoxymethoxy)-11-[(2R,5R,6R)-5-(methoxymethoxy)-6-tetradecyloxan-2-yl]undecyl]-5-methyl-3-phenylsulfanyloxolan-2-one
• CAS: 909270-52-6
• 化学式: C₅₃H₉₆O₁₀SSi
• 分子量: 953.491
• InChiKey: JFNQYLYLTUXMLO-YEWIPMEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.97
• 重原子数：
  65
• 可旋转键数：
  39
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2'R,5S,8'R,11'R,12'R,15'R,16'R)-3-[2'-(tert-butyldimethylsilanyloxy)-8',11',15'-(trimethoxymethoxy)-12',16'-oxidotriacontanyl]-5-methyl-3-phenylsulfanyldihydrofuran-2-one 在 盐酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 pyragonicin
  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：

  (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) sodium acetate 、 sodium hexamethyldisilazane 、 对甲苯磺酰肼 、 对苯醌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 9.08h， 生成 (2'R,5S,8'R,11'R,12'R,15'R,16'R)-3-[2'-(tert-butyldimethylsilanyloxy)-8',11',15'-(trimethoxymethoxy)-12',16'-oxidotriacontanyl]-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.