(2S,4R)-6,6-Dimethoxy-1-((4R,6R)-6-methyl-4-phenylsulfanyl-5,6-dihydro-4H-pyran-2-yl)-hexane-2,4-diol | 137166-28-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S,4R)-6,6-Dimethoxy-1-((4R,6R)-6-methyl-4-phenylsulfanyl-5,6-dihydro-4H-pyran-2-yl)-hexane-2,4-diol
• CAS: 137166-28-0
• 化学式: C₂₀H₃₀O₅S
• 分子量: 382.521
• InChiKey: YSAXRNDGMIQHAJ-YYAJDYIMSA-N

反应信息

• 作为反应物：
  描述：

  (2S,4R)-6,6-Dimethoxy-1-((4R,6R)-6-methyl-4-phenylsulfanyl-5,6-dihydro-4H-pyran-2-yl)-hexane-2,4-diol 在 N-碘代丁二酰亚胺 作用下， 生成 (2S,4S,8R)-2-(2,2-Dimethoxy-ethyl)-8-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-ol
  参考文献：
  名称：

  A route to unsaturated spiroketals from phenylthio hex-2-enopyranosides via sequential alkylation, allylic rearrangement and intramolecular glycosidation

  摘要：

  Alkylated phenylthio hex-2-enopyranosides readily undergo 1,3-phenylthio migration, and treatment of the resulting enol ether with N-iodosuccinimide gives an allyl-oxocarbenium ion which can be trapped intramolecularly by a suitably located hydroxy group to yield an unsaturated spiroketal.

  DOI：

  10.1039/c39910001207
• 作为产物：
  描述：

  (2R,6R)-2-Methyl-6-phenylsulfanyl-3,6-dihydro-2H-pyran 在 吡啶 、 正丁基锂 、 氢氟酸 作用下， 生成 (2S,4R)-6,6-Dimethoxy-1-((4R,6R)-6-methyl-4-phenylsulfanyl-5,6-dihydro-4H-pyran-2-yl)-hexane-2,4-diol
  参考文献：
  名称：

  A route to unsaturated spiroketals from phenylthio hex-2-enopyranosides via sequential alkylation, allylic rearrangement and intramolecular glycosidation

  摘要：

  Alkylated phenylthio hex-2-enopyranosides readily undergo 1,3-phenylthio migration, and treatment of the resulting enol ether with N-iodosuccinimide gives an allyl-oxocarbenium ion which can be trapped intramolecularly by a suitably located hydroxy group to yield an unsaturated spiroketal.

  DOI：

  10.1039/c39910001207

文献信息

• Ferrier Rearrangement under Nonacidic Conditions Based on Iodonium-Induced Rearrangements of Allylic n-Pentenyl Esters, n-Pentenyl Glycosides, and Phenyl Thioglycosides
  作者：J. Cristobal Lopez、Ana M. Gomez、Serafin Valverde、Bert Fraser-Reid

  DOI：10.1021/jo00117a042

  日期：1995.6