1,2-dideoxy-1,2-di-n-octylamino-D-(N)-β-glucoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-dideoxy-1,2-di-n-octylamino-D-(N)-β-glucoside
• 英文别名: (2R,3S,4R,5R,6R)-2-(hydroxymethyl)-5,6-bis(octylamino)oxane-3,4-diol
• 化学式: C₂₂H₄₆N₂O₄
• 分子量: 402.618
• InChiKey: HGLGFFLPCCHJFW-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  94
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-dideoxy-1,2-di-n-octylamino-D-(N)-β-glucoside 在 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 以95%的产率得到2-deoxy-2-n-octylamino-D-glucose
  参考文献：
  名称：

  Improved Method for the Synthesis of 2-Alkylamino-2-deoxy-d-glucopyranose and 1,2-Dialkylamino-1,2-dideoxy-d-(N)- β-glucoside

  摘要：

  An improved method for the synthesis of two types of carbohydrate-based, pH-sensitive surfactants has been developed. The surfactants are formed in almost quantitative yields from D-fructose and suitable alkylamines, when using a zinc halide salt as catalyst. The reaction proceeds via an initial Amadori reaction, and the 1,2-dialkylamino-1,2-dideoxy-D-(N)-beta-glucoside precipitates out of the reaction. The product can easily be hydrolyzed to the more water-soluble, surface-active, and pH-sensitive monoalkyl derivative 2-alkylarnino-2-deoxy-D-glucopyranose. Products from several amines can be prepared.

  DOI：

  10.1021/jo026461f
• 作为产物：
  描述：

  果糖 、 辛胺 在 4 A molecular sieve 、 zinc dibromide 作用下， 反应 48.0h， 以100%的产率得到1,2-dideoxy-1,2-di-n-octylamino-D-(N)-β-glucoside
  参考文献：
  名称：

  Improved Method for the Synthesis of 2-Alkylamino-2-deoxy-d-glucopyranose and 1,2-Dialkylamino-1,2-dideoxy-d-(N)- β-glucoside

  摘要：

  An improved method for the synthesis of two types of carbohydrate-based, pH-sensitive surfactants has been developed. The surfactants are formed in almost quantitative yields from D-fructose and suitable alkylamines, when using a zinc halide salt as catalyst. The reaction proceeds via an initial Amadori reaction, and the 1,2-dialkylamino-1,2-dideoxy-D-(N)-beta-glucoside precipitates out of the reaction. The product can easily be hydrolyzed to the more water-soluble, surface-active, and pH-sensitive monoalkyl derivative 2-alkylarnino-2-deoxy-D-glucopyranose. Products from several amines can be prepared.

  DOI：

  10.1021/jo026461f

文献信息

• Improved Method for the Synthesis of 2-Alkylamino-2-deoxy-<scp>d</scp>-glucopyranose and 1,2-Dialkylamino-1,2-dideoxy-<scp>d</scp>-(<i>N</i>)- β-glucoside
  作者：Peter S. Piispanen、Torbjörn Norin

  DOI：10.1021/jo026461f

  日期：2003.1.1

  An improved method for the synthesis of two types of carbohydrate-based, pH-sensitive surfactants has been developed. The surfactants are formed in almost quantitative yields from D-fructose and suitable alkylamines, when using a zinc halide salt as catalyst. The reaction proceeds via an initial Amadori reaction, and the 1,2-dialkylamino-1,2-dideoxy-D-(N)-beta-glucoside precipitates out of the reaction. The product can easily be hydrolyzed to the more water-soluble, surface-active, and pH-sensitive monoalkyl derivative 2-alkylarnino-2-deoxy-D-glucopyranose. Products from several amines can be prepared.