tert-Butyl-[(3aR,5S,6S,6aR)-5-(2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane | 137166-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: tert-Butyl-[(3aR,5S,6S,6aR)-5-(2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane
• CAS: 137166-23-5
• 化学式: C₂₅H₃₂O₈SSi
• 分子量: 520.676
• InChiKey: NLWHUIQUWLXNTP-KLARFABHSA-N

物化性质

• 沸点：
  564.2±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  tert-Butyl-[(3aR,5S,6S,6aR)-5-(2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane 在 吡啶 、 正丁基锂 、 硫酸 、 氢氟酸 、 水 作用下， 生成 (3aR,5R,6S,6aR)-2,2-Dimethyl-5-[(E)-2-((4R,6R)-6-methyl-4-phenylsulfanyl-5,6-dihydro-4H-pyran-2-yl)-vinyl]-tetrahydro-furo[2,3-d][1,3]dioxol-6-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