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相转移催化D-甘露醇合成1,2-甘油二酯

Phase transfer catalyzed synthesis of 1,2-diacylglycerol with D-mannitol as starting material

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【作者】 于荣华刘艳玲乔浩刘存礼

【Author】 YU Rong-hua,LIU Yan-ling,QIAO Hao,LIU Cun-li(Institute of Life Science and Pharmacy,Nanjing University of Technology,Nanjing 211816,China)

【机构】 南京工业大学生物与制药工程学院

【摘要】 以D-甘露醇为原料,经丙叉基保护、氧化还原、苄基保护、脱丙叉保护、醇的酰化、苄基的脱保护合成了1,2-甘油二酯,中间体和目标产物结构经过了IR和元素分析鉴定。考察了不同的萃取溶剂和相转移催化剂对重要中间体甘油醇缩丙酮合成的影响。最终采用价廉的、环境友好的乙酸乙酯作为萃取溶剂,相转移催化剂季铵盐四丁基硫酸氢铵的质量分数为0.1%时效果最佳,并选择了"一锅法"合成的路线。考察了缚酸剂对中间体3-氧-苄基甘油合成的影响。在最优条件下,实验选择有机碱三乙胺作为3-氧-苄基甘油合成的缚酸剂。最终1,2-甘油二酯产率达到49.3%。

【Abstract】 1,2-Diacylglycerol is synthesized by isopropylidene acetalformation,oxidation,benzylation,deprotection,acylation of alcohols and benzyl deprotection with D-mannitol as raw material.The chemical structures of intermediate and targeted product are characterized by IR and elemental analysis.The results are consistent with the molecular structures.The effects of extraction solvent and the phase transfer catalyst on the synthesis of the important intermediates 2,3-isopropylidene-sn-glycerol are investigated.The inexpensive,environmentally and friendly ethyl acetate is used as the extraction solvent.The optimal amount of phase transfer catalyst quaternary ammonium tetrabutyl ammonium hydrogen sulfate is 0.1%.The "one pot" synthesis route is selected.The effect of acid binding agent on the synthesis of 3-o-benzyl glycerol is also investigated.Under the optimized conditions,the final yield of 1,2-diacylglycerol is 49.3% with triethylamine as the acid binding agent.

  • 【文献出处】 现代化工 ,Modern Chemical Industry , 编辑部邮箱 ,2013年01期
  • 【分类号】TQ225.24
  • 【被引频次】3
  • 【下载频次】168
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