(2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran | 886852-55-7

• 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,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran
• 英文别名: 3-[(2S,3R,6R)-3-azido-6-phenylmethoxy-3,6-dihydro-2H-pyran-2-yl]propoxy-tert-butyl-dimethylsilane
• CAS: 886852-55-7
• 化学式: C₂₁H₃₃N₃O₃Si
• 分子量: 403.597
• InChiKey: XXNYIXAQVMASMH-HSALFYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran 在 四氧化锇 、 对甲苯磺酸 水 、 N-甲基吗啉氧化物 作用下， 以 丙酮 、 叔丁醇 为溶剂， 反应 24.5h， 生成 (3-((3aR,4R,6S,7S,7aR)-7-azido-4-(benzyloxy)-tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)propoxy)(tert-butyl)dimethylsilane
  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：

  (2S,3R,6R)-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3-ol 在 bis(η3-allyl-μ-chloropalladium(II)) 、 1,4-双(二苯基膦)丁烷 吡啶 、 4-二甲氨基吡啶 、 叠氮基三甲基硅烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2S,3R,6R)-3-azido-6-(benzyloxy)-3,6-dihydro-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran
  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.