3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate | 886852-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate
• 英文别名: 3-[(2S,3R,4R,5R,6R)-3-azido-4,5-dihydroxy-6-phenylmethoxyoxan-2-yl]propyl methanesulfonate
• CAS: 886852-54-6
• 化学式: C₁₆H₂₃N₃O₇S
• 分子量: 401.441
• InChiKey: HDUADCSFKLBJAH-AALSBFMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、689.47 kPa 条件下， 反应 72.0h， 以88%的产率得到(1R,2S,8S,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol
  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 四氧化锇 、 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 、 四丁基氟化铵 、 水 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 反应 84.5h， 生成 3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate
  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.