1-O-benzyl-2-O-(2-methoxyethoxymethyl)-L-threitol | 186754-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-benzyl-2-O-(2-methoxyethoxymethyl)-L-threitol
• CAS: 186754-12-1
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: HWHKTGOJONDMEB-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  21.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-O-benzyl-2-O-(2-methoxyethoxymethyl)-L-threitol 在 吡啶 、 四氯化钛 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 192.5h， 生成 (3aS,4R,6R,6aS)-4-((1R,2S)-1-Benzyloxymethyl-2,3-bis-octyloxy-propoxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole
  参考文献：
  名称：

  New 2/2-type surfactants via anomeric O-alkylation of mannofuranose

  摘要：

  New 2/2-type surfactants were synthesized from 1,2-di-O-alkyl-4-O-benzyl-L-threitols and 1,3-di-O-alkyl-4-O-benzyl-D-threitols. Their transformation into trifluoromethanesulfonates and then reaction with 2,3:5,6-di-O-isopropylidene-D-mannofuranose gave, via anomeric O-alkylation, predominantly beta-D-mannofuranosides of erythritol. Hydrogenolytic O-debenzylation furnished the 4-O-deprotected derivatives which, on reaction with sulfur trioxide-trimethylamine and then hydrolytic removal of the O-isopropylidene groups, afforded 2/2-type surfactants having a mannofuranose and a sulfate residue as head groups. The 4-O-deprotected derivatives were also transformed into the corresponding 4-tosylates and the 4-iodides as alkylating agents. Their reaction with tetraethylene glycol, diethyl malonate, and diethyl iminodiacetate and then removal of the protective groups furnished 2/2-type surfactants having a mannofuranose residue and a tetraethylene glycol, or a malonate, or an iminodiacetate residue, respectively, as head groups. Surface tension and critical micelle concentration measurements with these compounds exhibited interesting amphiphilic properties. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00272-8
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-O-benzyl-2-O-(2-methoxyethoxymethyl)-L-threitol
  参考文献：
  名称：

  New 2/2-type surfactants via anomeric O-alkylation of mannofuranose

  摘要：

  New 2/2-type surfactants were synthesized from 1,2-di-O-alkyl-4-O-benzyl-L-threitols and 1,3-di-O-alkyl-4-O-benzyl-D-threitols. Their transformation into trifluoromethanesulfonates and then reaction with 2,3:5,6-di-O-isopropylidene-D-mannofuranose gave, via anomeric O-alkylation, predominantly beta-D-mannofuranosides of erythritol. Hydrogenolytic O-debenzylation furnished the 4-O-deprotected derivatives which, on reaction with sulfur trioxide-trimethylamine and then hydrolytic removal of the O-isopropylidene groups, afforded 2/2-type surfactants having a mannofuranose and a sulfate residue as head groups. The 4-O-deprotected derivatives were also transformed into the corresponding 4-tosylates and the 4-iodides as alkylating agents. Their reaction with tetraethylene glycol, diethyl malonate, and diethyl iminodiacetate and then removal of the protective groups furnished 2/2-type surfactants having a mannofuranose residue and a tetraethylene glycol, or a malonate, or an iminodiacetate residue, respectively, as head groups. Surface tension and critical micelle concentration measurements with these compounds exhibited interesting amphiphilic properties. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00272-8