(4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane | 172293-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane
• CAS: 172293-71-9
• 化学式: C₂₂H₂₈O₅Si
• 分子量: 400.547
• InChiKey: YGVGXHZVJPUELM-SBHAEUEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane 在 吡啶 、 正丁基锂 、 三甲基铝 、 六甲基二硅氮烷 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 15.92h， 生成 (3R,4S,5R)-6-<(tert-Butyldiphenylsilyl)oxy>-3,4,5-tris<(trimethylsilyl)oxy>-1-(2'-thiazolyl)-1-hexanone
  参考文献：
  名称：

  Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative

  摘要：

  The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a noncarbohydrate precursor was achieved in six steps (19% yield) from a chiral, gamma,delta-epoxy beta-hydroxy ester, 3a, readily available from the corresponding alpha,beta-epoxy aldehyde. The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.

  DOI：

  10.1021/jo00127a047
• 作为产物：
  描述：

  tert-Butyl (3R,4R,5R)-6-<(tert-butyldiphenylsilyl)oxy>-4,5-epoxy-3-hydroxyhexanoate 在 三甲基氯硅烷 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以96%的产率得到(4R,5S,1'R)-5-<2'-<(tert-Butyldiphenylsilyl)oxy>-1'-hydroxyethyl>-4-hydroxy-2-oxo-1-oxacyclopentane
  参考文献：
  名称：

  Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative

  摘要：

  The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a noncarbohydrate precursor was achieved in six steps (19% yield) from a chiral, gamma,delta-epoxy beta-hydroxy ester, 3a, readily available from the corresponding alpha,beta-epoxy aldehyde. The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.

  DOI：

  10.1021/jo00127a047