(3aR,4R,6S,6aS)-4-allyl-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole | 1180540-47-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,6S,6aS)-4-allyl-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
• 英文别名: (3aS,4S,6R,6aR)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-prop-2-enyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
• CAS: 1180540-47-9
• 化学式: C₁₅H₂₅NO₄
• 分子量: 283.368
• InChiKey: BNTYMOSVCDTYTL-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (3aR,4R,6S,6aS)-4-allyl-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(3aR,4R,6S,6aS)-tert-butyl 4-allyl-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate
  参考文献：
  名称：

  A Versatile Access to Calystegine Analogues as Potential Glycosidases Inhibitors

  摘要：

  An efficient metathetic strategy and nitrone chemistry have been suitably tethered to construct 8-azabicyclo[3.2.1]octanes as versatile precursors for the synthesis of several calystegine analogues. This synthetic strategy relies on the ability of mannose-derived nitrone to undergo a highly stereoselective nucleophilic addition of various Grignard reagents to access syn orientation of alkenes, which then smoothly undergo ring-closing metathesis (RCM) to provide this framework. These RCM products 18 and 20 have been successfully used as advance precursors to synthesize many calystegine analogues (27, 36, 38, 40, 43, and 44) either by syn-dihydroxylation or by hydrogenation and followed by global deprotection. Interestingly, both compounds 36 and 40 exhibited significant noncompetitive inhibition against alpha-mannosidase and N-acetyl-beta-D-glucosaminidase.

  DOI：

  10.1021/jo901342w
• 作为产物：
  描述：

  (3aR,4R,6S,6aS)-4-allyl-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5(4H)-ol 在 indium 、 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 以84%的产率得到(3aR,4R,6S,6aS)-4-allyl-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
  参考文献：
  名称：

  A Versatile Access to Calystegine Analogues as Potential Glycosidases Inhibitors

  摘要：

  An efficient metathetic strategy and nitrone chemistry have been suitably tethered to construct 8-azabicyclo[3.2.1]octanes as versatile precursors for the synthesis of several calystegine analogues. This synthetic strategy relies on the ability of mannose-derived nitrone to undergo a highly stereoselective nucleophilic addition of various Grignard reagents to access syn orientation of alkenes, which then smoothly undergo ring-closing metathesis (RCM) to provide this framework. These RCM products 18 and 20 have been successfully used as advance precursors to synthesize many calystegine analogues (27, 36, 38, 40, 43, and 44) either by syn-dihydroxylation or by hydrogenation and followed by global deprotection. Interestingly, both compounds 36 and 40 exhibited significant noncompetitive inhibition against alpha-mannosidase and N-acetyl-beta-D-glucosaminidase.

  DOI：

  10.1021/jo901342w

文献信息

• A Versatile Access to Calystegine Analogues as Potential Glycosidases Inhibitors
  作者：Krishna P. Kaliappan、Prasanta Das、Sanjay T. Chavan、Sushma G. Sabharwal

  DOI：10.1021/jo901342w

  日期：2009.8.21

  An efficient metathetic strategy and nitrone chemistry have been suitably tethered to construct 8-azabicyclo[3.2.1]octanes as versatile precursors for the synthesis of several calystegine analogues. This synthetic strategy relies on the ability of mannose-derived nitrone to undergo a highly stereoselective nucleophilic addition of various Grignard reagents to access syn orientation of alkenes, which then smoothly undergo ring-closing metathesis (RCM) to provide this framework. These RCM products 18 and 20 have been successfully used as advance precursors to synthesize many calystegine analogues (27, 36, 38, 40, 43, and 44) either by syn-dihydroxylation or by hydrogenation and followed by global deprotection. Interestingly, both compounds 36 and 40 exhibited significant noncompetitive inhibition against alpha-mannosidase and N-acetyl-beta-D-glucosaminidase.