(2S,3S,R(S))-tert-butyldiphenyl{2-[3-(p-tolylsulfinyl)-3,6-dihydro-2H-pyran-2-yl]ethoxy}silane | 1082073-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,R(S))-tert-butyldiphenyl{2-[3-(p-tolylsulfinyl)-3,6-dihydro-2H-pyran-2-yl]ethoxy}silane
• CAS: 1082073-87-7
• 化学式: C₃₀H₃₆O₃SSi
• 分子量: 504.766
• InChiKey: JRNWPDVFZVNHND-DMUKBKCISA-N

反应信息

• 作为反应物：
  描述：

  (2S,3S,R(S))-tert-butyldiphenyl{2-[3-(p-tolylsulfinyl)-3,6-dihydro-2H-pyran-2-yl]ethoxy}silane 在 三甲氧基磷 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以83%的产率得到(-)-(3R,6S)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  [2,3]-Sigmatropic Rearrangements of 3-Sulfinyl Dihydropyrans: Application to the Syntheses of the Cores of ent-Dysiherbaine and Deoxymalayamicin A

  摘要：

  The [2,3]-sigmatropic rearrangement of a variety of configurationally stable diastereomeric allylic sulfinyl dihydropyrans, produced by base-promoted cyclization of sulfinyl dienols, has been studied. In some cases, the efficient transformation of these substrates into dihydropyranols required an in-depth study of reaction conditions, with the preferred protocol relying on the use of DABCO in warm toluene. This methodology has been applied to the syntheses of the cores of ent-dysiherbaine and deoxymalayamicin A by means of efficient tethered aminohydroxylations.

  DOI：

  10.1021/jo8015709
• 作为产物：
  描述：

  (-)-(S,2Z,4Z)-7-(tert-butyldiphenylsilyloxy)-4-(p-tolylsulfinyl)hepta-2,4-dien-1-ol 在 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2⁽⁵⁾,4⁽⁵⁾-catenadi(phosphazene) 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 以41%的产率得到(-)-(2S,3R,R(S))-tert-butyldiphenyl{2-[3-(p-tolylsulfinyl)-3,6-dihydro-2H-pyran-2-yl]ethoxy}silane
  参考文献：
  名称：

  [2,3]-Sigmatropic Rearrangements of 3-Sulfinyl Dihydropyrans: Application to the Syntheses of the Cores of ent-Dysiherbaine and Deoxymalayamicin A

  摘要：

  The [2,3]-sigmatropic rearrangement of a variety of configurationally stable diastereomeric allylic sulfinyl dihydropyrans, produced by base-promoted cyclization of sulfinyl dienols, has been studied. In some cases, the efficient transformation of these substrates into dihydropyranols required an in-depth study of reaction conditions, with the preferred protocol relying on the use of DABCO in warm toluene. This methodology has been applied to the syntheses of the cores of ent-dysiherbaine and deoxymalayamicin A by means of efficient tethered aminohydroxylations.

  DOI：

  10.1021/jo8015709