methyl 2-(tert-butyldimethylsilanyloxymethyl)-6-(1-ethoxyethoxy)-3,6-dihydro-2H-pyran-3-yl carbonate | 1260507-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 2-(tert-butyldimethylsilanyloxymethyl)-6-(1-ethoxyethoxy)-3,6-dihydro-2H-pyran-3-yl carbonate
• 英文别名: [(2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(1-ethoxyethoxy)-3,6-dihydro-2H-pyran-3-yl] methyl carbonate
• CAS: 1260507-73-0
• 化学式: C₁₈H₃₄O₇Si
• 分子量: 390.549
• InChiKey: CZZLKQRPHVWRFL-MYLOQMAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-(tert-butyldimethylsilanyloxymethyl)-6-(1-ethoxyethoxy)-3,6-dihydro-2H-pyran-3-yl carbonate 、 苄胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以71%的产率得到benzyl-[2-(tert-butyldimethylsilanyloxymethyl)-6-(1-ethoxyethoxy)-3,6-dihydro-2H-pyran-3-yl]-amine
  参考文献：
  名称：

  Synthesis of chiral unsaturated aminolactones using Pd-catalyzed allylic amination

  摘要：

  Stereoselective synthesis of (5R,6R)- and (5S,6S)-5-benzylamino-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydropyran-2-ones starting from D-glucal and furanaldehyde, respectively, is described. The synthesis relies on a Sharpless asymmetric dihydroxylation, an Achmatowicz reaction, and a stereoselective Pd-catalyzed allylic amination as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.09.003
• 作为产物：
  描述：

  2-(tert-butyl-dimethylsilanyloxymethyl)-6-(1-ethoxyethoxy)-3,6-dihydro-2H-pyran-3-ol 、 氯甲酸甲酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以1.15 g的产率得到methyl 2-(tert-butyldimethylsilanyloxymethyl)-6-(1-ethoxyethoxy)-3,6-dihydro-2H-pyran-3-yl carbonate
  参考文献：
  名称：

  Synthesis of chiral unsaturated aminolactones using Pd-catalyzed allylic amination

  摘要：

  Stereoselective synthesis of (5R,6R)- and (5S,6S)-5-benzylamino-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydropyran-2-ones starting from D-glucal and furanaldehyde, respectively, is described. The synthesis relies on a Sharpless asymmetric dihydroxylation, an Achmatowicz reaction, and a stereoselective Pd-catalyzed allylic amination as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.09.003

文献信息

• Synthesis of chiral unsaturated aminolactones using Pd-catalyzed allylic amination
  作者：Annukka Kallinen、Jan Tois、Rainer Sjöholm、Robert Franzén

  DOI：10.1016/j.tetasy.2010.09.003

  日期：2010.10

  Stereoselective synthesis of (5R,6R)- and (5S,6S)-5-benzylamino-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydropyran-2-ones starting from D-glucal and furanaldehyde, respectively, is described. The synthesis relies on a Sharpless asymmetric dihydroxylation, an Achmatowicz reaction, and a stereoselective Pd-catalyzed allylic amination as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.