(2R,5S,6R)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yl pivalate | 1304445-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,5S,6R)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yl pivalate
• 英文别名: [(2R,3S,6R)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl] 2,2-dimethylpropanoate
• CAS: 1304445-94-0
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: KVVHKEKBTOUBED-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,5S,6R)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yl pivalate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 2-硝基苯磺酰肼 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2R,5S,6R)-4-((2'S,6'R)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yloxy)-3,4,5,6-tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl pivalate
  参考文献：
  名称：

  De Novo Asymmetric Approach to the Disaccharide Portion of SCH-47554

  摘要：

  A method for the asymmetric synthesis of the disaccharide portion of SCH-47554 has been developed in 6 steps. The route is shorter than the reported route to a related disaccharide. The route involves the use of the Noyori reduction to establish the asymmetry of the D- and L-sugar portion of the molecule. Diastereoselective Pd-glycosylation reaction and subsequent post-glycosylation transformation are used to establish the remaining stereocenter.

  DOI：

  10.3987/com-10-s(e)114
• 作为产物：
  描述：

  (2R)-6-hydroxy-2-methyl-2H-pyran-3(6)-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2R,5S,6R)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yl pivalate
  参考文献：
  名称：

  De Novo Asymmetric Approach to the Disaccharide Portion of SCH-47554

  摘要：

  A method for the asymmetric synthesis of the disaccharide portion of SCH-47554 has been developed in 6 steps. The route is shorter than the reported route to a related disaccharide. The route involves the use of the Noyori reduction to establish the asymmetry of the D- and L-sugar portion of the molecule. Diastereoselective Pd-glycosylation reaction and subsequent post-glycosylation transformation are used to establish the remaining stereocenter.

  DOI：

  10.3987/com-10-s(e)114

文献信息

• De Novo Asymmetric Approach to the Disaccharide Portion of SCH-47554
  作者：George A. O'Doherty、Miaosheng Li、Xiaomei Yu

  DOI：10.3987/com-10-s(e)114

  日期：——

  A method for the asymmetric synthesis of the disaccharide portion of SCH-47554 has been developed in 6 steps. The route is shorter than the reported route to a related disaccharide. The route involves the use of the Noyori reduction to establish the asymmetry of the D- and L-sugar portion of the molecule. Diastereoselective Pd-glycosylation reaction and subsequent post-glycosylation transformation are used to establish the remaining stereocenter.