ethyl 2-[(2S,3R,4S,6S)-6-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]-3-methyloxan-2-yl]acetate | 215317-72-9

• 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: ethyl 2-[(2S,3R,4S,6S)-6-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]-3-methyloxan-2-yl]acetate
• CAS: 215317-72-9
• 化学式: C₁₉H₂₈O₆
• 分子量: 352.428
• InChiKey: VGPLBIMECYFYQO-QCSYZSNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(2S,3R,4S,6S)-6-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]-3-methyloxan-2-yl]acetate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到ethyl 2-[(2S,3R,4S,6S)-6-formyl-4-[(4-methoxyphenyl)methoxy]-3-methyloxan-2-yl]acetate
  参考文献：
  名称：

  A Modular Enantioselective Approach to Construction of the Macrolactone Core of Polycavernoside A

  摘要：

  A program directed toward a total synthesis of polycavernoside A is described. The synthesis of five building blocks is detailed. The first of two electrophilic units, the lactone 3, was prepared in four steps from the known enantiomerically pure oxirane 15. Pyranyl aldehyde 5 was elaborated in turn from L-malic acid via 10. While the route to 30 involved 3 as a starting material, dithiane 2 was obtained in a straightforward manner from 10 as well. The merging of the chiral sectors could not be accomplished by way of the lithiated dithianyl anions, presumably as a consequence of their heightened basicity. The strategic incorporation of the trienyl sector was accomplished, although no attempt was made to control the diastereoselectivity of the process.

  DOI：

  10.1021/jo981083t
• 作为产物：
  描述：

  (3R,4S,6S)-6-((Tert-butyldiphenylsilyloxy)methyl)-4-(4-methoxybenzyloxy)-3-methyltetrahydro-2H-pyran-2-one 在 三乙基硅烷 、 三氟甲磺酸 、 四丁基氟化铵 、 四氯化钛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl 2-[(2S,3R,4S,6S)-6-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]-3-methyloxan-2-yl]acetate
  参考文献：
  名称：

  A Modular Enantioselective Approach to Construction of the Macrolactone Core of Polycavernoside A

  摘要：

  A program directed toward a total synthesis of polycavernoside A is described. The synthesis of five building blocks is detailed. The first of two electrophilic units, the lactone 3, was prepared in four steps from the known enantiomerically pure oxirane 15. Pyranyl aldehyde 5 was elaborated in turn from L-malic acid via 10. While the route to 30 involved 3 as a starting material, dithiane 2 was obtained in a straightforward manner from 10 as well. The merging of the chiral sectors could not be accomplished by way of the lithiated dithianyl anions, presumably as a consequence of their heightened basicity. The strategic incorporation of the trienyl sector was accomplished, although no attempt was made to control the diastereoselectivity of the process.

  DOI：

  10.1021/jo981083t

文献信息

• A Modular Enantioselective Approach to Construction of the Macrolactone Core of Polycavernoside A
  作者：Leo A. Paquette、Dmitri Pissarnitski、Louis Barriault

  DOI：10.1021/jo981083t

  日期：1998.10.1

  A program directed toward a total synthesis of polycavernoside A is described. The synthesis of five building blocks is detailed. The first of two electrophilic units, the lactone 3, was prepared in four steps from the known enantiomerically pure oxirane 15. Pyranyl aldehyde 5 was elaborated in turn from L-malic acid via 10. While the route to 30 involved 3 as a starting material, dithiane 2 was obtained in a straightforward manner from 10 as well. The merging of the chiral sectors could not be accomplished by way of the lithiated dithianyl anions, presumably as a consequence of their heightened basicity. The strategic incorporation of the trienyl sector was accomplished, although no attempt was made to control the diastereoselectivity of the process.