(-)-(3aS,6S,7R,7aS)-7-hydroxy-6-(2-hydroxyethyl)tetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one | 1082074-15-4

• 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: (-)-(3aS,6S,7R,7aS)-7-hydroxy-6-(2-hydroxyethyl)tetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one
• 英文别名: (3aS,6S,7R,7aS)-7-hydroxy-6-(2-hydroxyethyl)-1,3a,4,6,7,7a-hexahydropyrano[4,3-d][1,3]oxazol-2-one
• CAS: 1082074-15-4
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: JCFKRBZXSDYNOH-WNJXEPBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(3aS,6S,7R,7aS)-7-hydroxy-6-(2-hydroxyethyl)tetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以34%的产率得到(-)-(3aS,5aS,8aR,8bR)-hexahydro-2H-furo[2',3':5,6]pyrano[4,3-d][1,3]oxazole-2,7(1H)-dione
  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：

  (-)-(3aS,6S,7R,7aS)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-hydroxytetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one 在 dowex 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以84%的产率得到(-)-(3aS,6S,7R,7aS)-7-hydroxy-6-(2-hydroxyethyl)tetrahydro-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

文献信息

• [2,3]-Sigmatropic Rearrangements of 3-Sulfinyl Dihydropyrans: Application to the Syntheses of the Cores of <i>ent</i>-Dysiherbaine and Deoxymalayamicin A
  作者：Roberto Fernández de la Pradilla、Nadia Lwoff、Miguel Ángel del Águila、Mariola Tortosa、Alma Viso

  DOI：10.1021/jo8015709

  日期：2008.11.21

  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.