(+)-(3aR,6S,7S,7aR)-6-n-butyl-7-hydroxytetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one | 960405-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (+)-(3aR,6S,7S,7aR)-6-n-butyl-7-hydroxytetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one
• CAS: 960405-00-9
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: KOLKLZVSDYBKGN-XSPKLOCKSA-N

反应信息

• 作为反应物：
  描述：

  (+)-(3aR,6S,7S,7aR)-6-n-butyl-7-hydroxytetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one 、 碘甲烷 在 barium hydroxide octahydrate 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 以66%的产率得到(+)-(3aR,6S,7S,7aR)-6-n-butyl-7-hydroxy-1-methyltetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one
  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：

  (-)-(3R,6S)-6-n-butyl-3,6-dihydro-2H-pyran-3-yl carbamate 在 potassium osmate(VI) dihydrate 、 sodium hydroxide 、 次氯酸叔丁酯 、 N,N-二异丙基乙胺 作用下， 以 丙醇 、 水 为溶剂， 反应 21.0h， 以24%的产率得到(+)-(3aR,6S,7S,7aR)-6-n-butyl-7-hydroxytetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one
  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