(2S,6R)-6-(benzyloxy)-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one | 886852-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,6R)-6-(benzyloxy)-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one
• 英文别名: (2R,6S)-6-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-2-phenylmethoxy-2H-pyran-5-one
• CAS: 886852-59-1
• 化学式: C₂₁H₃₂O₄Si
• 分子量: 376.568
• InChiKey: VXMGQTAMIVVJTE-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,6R)-6-(benzyloxy)-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以94%的产率得到(2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-ol
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of d- and l-Swainsonine

  摘要：

  The enantioselective syntheses of both enantiomers of the indolizidine natural product swainsonine have been achieved in 13 steps from furan. The indolizidine ring system is installed by a one-pot hydrogenolysis of both an azide and an O-Bn group along with an intramolecular reductive amination reaction. The asymmetry of swainsonine was introduced by Noyori reduction of an acylfuran. This route relies upon an Achmatowicz rearrangement, a diastereoselective palladium-catalyzed glycosylation, Luche reduction, and a dihydroxylation reaction.

  DOI：

  10.1021/ol0602811
• 作为产物：
  描述：

  1-(呋喃-2-基)-4-羟基丁烷-1-酮 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 (1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine-ruthenium(mesitylene) 、 sodium acetate 、 三苯基膦 咪唑 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 甲酸 、 水 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.5h， 生成 (2S,6R)-6-(benzyloxy)-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of d- and l-Swainsonine

  摘要：

  The enantioselective syntheses of both enantiomers of the indolizidine natural product swainsonine have been achieved in 13 steps from furan. The indolizidine ring system is installed by a one-pot hydrogenolysis of both an azide and an O-Bn group along with an intramolecular reductive amination reaction. The asymmetry of swainsonine was introduced by Noyori reduction of an acylfuran. This route relies upon an Achmatowicz rearrangement, a diastereoselective palladium-catalyzed glycosylation, Luche reduction, and a dihydroxylation reaction.

  DOI：

  10.1021/ol0602811

文献信息

• De Novo Asymmetric Synthesis of <scp>d</scp>- and <scp>l</scp>-Swainsonine
  作者：Haibing Guo、George A. O'Doherty

  DOI：10.1021/ol0602811

  日期：2006.4.1

  The enantioselective syntheses of both enantiomers of the indolizidine natural product swainsonine have been achieved in 13 steps from furan. The indolizidine ring system is installed by a one-pot hydrogenolysis of both an azide and an O-Bn group along with an intramolecular reductive amination reaction. The asymmetry of swainsonine was introduced by Noyori reduction of an acylfuran. This route relies upon an Achmatowicz rearrangement, a diastereoselective palladium-catalyzed glycosylation, Luche reduction, and a dihydroxylation reaction.