6-azido-5-tert-butyldimethylsilyloxy-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone | 261722-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6-azido-5-tert-butyldimethylsilyloxy-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone
• 英文别名: (5S)-5-[(1R)-2-azido-1-[tert-butyl(dimethyl)silyl]oxyethyl]oxolan-2-one
• CAS: 261722-05-8
• 化学式: C₁₂H₂₃N₃O₃Si
• 分子量: 285.418
• InChiKey: WTAJFMGEZKMVBN-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-azido-5-tert-butyldimethylsilyloxy-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone 在 palladium on activated charcoal 盐酸 、 三氯化铝 、 氢气 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， -20.0~20.0 ℃ 、5.0 MPa 条件下， 反应 16.17h， 生成 (5S,6R)-5,6-O-isopropylidene-azepane-2-one
  参考文献：
  名称：

  Studies on the synthesis of chiral nonracemic 3,4-disubstituted azepanes, a formal synthesis of (+)- and (−)-balanol

  摘要：

  Sugar lactones were converted to 3,4-disubstituted azepanes and caprolactam derivatives by selective deoxygenation, functionalization and reductive cyclization. The cyclization proved troublesome with 6-azidolactols but led to good results with the corresponding lactones. A formal synthesis of (+)- and (-)-balanol is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00466-8
• 作为产物：
  描述：

  6-bromo-5-tert-butyldimethylsilyloxy-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以67%的产率得到6-azido-5-tert-butyldimethylsilyloxy-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone
  参考文献：
  名称：

  Studies on the synthesis of chiral nonracemic 3,4-disubstituted azepanes, a formal synthesis of (+)- and (−)-balanol

  摘要：

  Sugar lactones were converted to 3,4-disubstituted azepanes and caprolactam derivatives by selective deoxygenation, functionalization and reductive cyclization. The cyclization proved troublesome with 6-azidolactols but led to good results with the corresponding lactones. A formal synthesis of (+)- and (-)-balanol is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00466-8

文献信息

• Studies on the synthesis of chiral nonracemic 3,4-disubstituted azepanes, a formal synthesis of (+)- and (−)-balanol
  作者：Claus Herdeis、Rafat M Mohareb、Reinhard B Neder、Franz Schwabenländer、Joachim Telser

  DOI：10.1016/s0957-4166(99)00466-8

  日期：1999.12

  Sugar lactones were converted to 3,4-disubstituted azepanes and caprolactam derivatives by selective deoxygenation, functionalization and reductive cyclization. The cyclization proved troublesome with 6-azidolactols but led to good results with the corresponding lactones. A formal synthesis of (+)- and (-)-balanol is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.