2-{(2R,3S)-2-[(3aS,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-3,4-bis-octyloxy-butyl}-malonic acid diethyl ester | 186754-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-{(2R,3S)-2-[(3aS,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-3,4-bis-octyloxy-butyl}-malonic acid diethyl ester
• CAS: 186754-44-9
• 化学式: C₃₉H₇₀O₁₂
• 分子量: 730.978
• InChiKey: QKIJBUXYUNODJK-ORAYASGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.02
• 重原子数：
  51.0
• 可旋转键数：
  27.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  126.44
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-{(2R,3S)-2-[(3aS,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-3,4-bis-octyloxy-butyl}-malonic acid diethyl ester 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 2-{(2R,3S)-2-[(2R,3S,4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-3,4-bis-octyloxy-butyl}-malonic acid diethyl ester
  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：

  1-O-benzyl-2-O-(2-methoxyethoxymethyl)-3,4-di-O-octyl-L-threitol 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium ethanolate 、 四氯化钛 、 sodium hydride 作用下， 以 吡啶 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 20.5h， 生成 2-{(2R,3S)-2-[(3aS,4R,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-3,4-bis-octyloxy-butyl}-malonic acid diethyl ester
  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