3,6-dideoxy-3-(N,N-diethylamino)-D-gulal | 1207632-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-dideoxy-3-(N,N-diethylamino)-D-gulal
• 英文别名: (2R,3R,4S)-4-(diethylamino)-2-methyl-3,4-dihydro-2H-pyran-3-ol
• CAS: 1207632-79-8
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: AHOUWIPOXWEGHS-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-O-mesyl-6-deoxy-D-glucal 、 二乙胺 在 potassium tert-butylate 作用下， 反应 1.0h， 以69%的产率得到3,6-dideoxy-3-(N,N-diethylamino)-D-gulal
  参考文献：
  名称：

  Aminolysis of glycal-derived allyl epoxides and activated aziridines. Effects of the absence of coordination processes on the regio- and stereoselectivity

  摘要：

  The addition of primary and secondary aliphatic amines to glycal-derived allyl epoxides is completely 1,2-regio- and anti-stereoselective, whereas mixtures of the corresponding anti-1,2- [3-N-(substituted-amino) glycals] and anti-1,4-addition products (N-glycosyl amines) are obtained with N-(mesyl)-aziridines. In this way, structural moieties, otherwise difficult to synthesize, are obtained by means of a very simple protocol. The regio- and stereoselectivity observed with epoxides is the consequence of an isomerization process, whereas the result obtained with aziridines is explained by the absence of an effective substrate-nucleophile (amine) coordination. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.059