(5S)-3-[(R)-2-(tert-butyldimethylsilyloxy)non-8-enyl]-5-methyl-3-phenylthio-3H-dihydrofuran-2-one | 862603-33-6

• 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)-3-[(R)-2-(tert-butyldimethylsilyloxy)non-8-enyl]-5-methyl-3-phenylthio-3H-dihydrofuran-2-one
• 英文别名: (5S)-3-[(2R)-2-[tert-butyl(dimethyl)silyl]oxynon-8-enyl]-5-methyl-3-phenylsulfanyloxolan-2-one
• CAS: 862603-33-6
• 化学式: C₂₆H₄₂O₃SSi
• 分子量: 462.769
• InChiKey: OEBAOTPMNPCAJV-SMWUWQHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.77
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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)-3-[(R)-2-(tert-butyldimethylsilyloxy)non-8-enyl]-5-methyl-3-phenylthio-3H-dihydrofuran-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium acetate 、 magnesium monoperoxyphthalate hexahydrate 、 乙酰氯 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 (+)-rollimembrin
  参考文献：
  名称：

  Stereoselective Syntheses of Rolliniastatin 1, Rollimembrin, and Membranacin

  摘要：

  A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).

  DOI：

  10.1021/ja0526867
• 作为产物：
  描述：

  6-溴-1-己烯 在 2,6-二甲基吡啶 、 sodium iodide 、 magnesium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 乙基苯 、 丙酮 为溶剂， 反应 76.5h， 生成 (5S)-3-[(R)-2-(tert-butyldimethylsilyloxy)non-8-enyl]-5-methyl-3-phenylthio-3H-dihydrofuran-2-one
  参考文献：
  名称：

  Total Synthesis of (+)-cis-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium

  摘要：

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.

  DOI：

  10.1021/ja0660148

文献信息

• Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-<i>cis</i>-Sylvaticin
  作者：Timothy J. Donohoe、Robert M. Harris、Oliver Williams、Gráinne C. Hargaden、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja9049959

  日期：2009.9.9

  Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.
• Stereoselective Syntheses of Rolliniastatin 1, Rollimembrin, and Membranacin
  作者：Gyochang Keum、Cheol Hee Hwang、Soon Bang Kang、Youseung Kim、Eun Lee

  DOI：10.1021/ja0526867

  日期：2005.7.1

  A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).
• Total Synthesis of (+)-<i>cis</i>-Sylvaticin:  Double Oxidative Cyclization Reactions Catalyzed by Osmium
  作者：Timothy J. Donohoe、Robert M. Harris、Jeremy Burrows、Jeremy Parker

  DOI：10.1021/ja0660148

  日期：2006.10.1

  The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.