PTC法合成杂环羧酸类1-O-芳酰基-2,3,4,6-四-O-乙酰基-β-D-吡喃己糖化合物的研究  

Study of Synthesis of 1-O-Aroyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoses of Heterocyclic Carboxylic Acids by PTC Method

作　　者：陈勇[1] 周国平[1] 梁俊[1] 马燕东[1] 

机构地区：[1]江苏工业学院化学工程系,江苏常州213164

出　　处：《江苏工业学院学报》2007年第1期9-13,共5页Journal of Jiangsu Polytechnic University

摘　　要：以十六烷基三甲基溴化铵作为相转移催化剂,用2,3,4,6-四-O-乙酰基-α-D-溴代吡喃葡萄糖与杂环羧酸反应,合成了相应的1-O-芳酰基-2,3,4,6-四-O-乙酰基-β-D-吡喃己糖。初步结果显示当碳酸钾与杂环羧酸物质的量比为2.0∶1时,反应温度为50℃时,反应时间为5 h时,收率较好。另外通过解析这些化合物IR、1HNMR确证了这些1-O-芳酰基-2,3,4,6-四-O-乙酰基-β-D-吡喃己糖化合物的结构,确证其糖苷键构型均为β型异构。该相转移催化法具有反应条件温和,后处理简单和立体选择性强等优点。Seven 1- O- Aroyl- 2,3,4,6 -tetra- O -acetyl -β- D-glucopyranoses of heterocyclic carboxylic acids were synthesized by reaction of 2,3,4,6 - tetra - O- acetyl-α- D- glucopyranosyl bromide with corresponding heterocyclic carboxylic acid using cetyltrimethyl ammonium bromide as a phase-transfer catalyst. The preliminary results showed that when the molar ratio of potassium carbonate to heterocyclic carboxylic acid was 2.0 ： 1, the reaction temperature was 50 ℃and reaction time was 5 h, the yield was good. In the IR spectra of these products, the absorption of bending vibration of C1- H bond in glycosyl-ring appears at about 910 cm^-1. In the ^1HNMR spectra of the products, the chemical shift of C1- H in glycosyl-ring appears at downfield, the coupling constant J1-2 =7.0-7.5. The IR,IHNMR spectra comfirmed their β-anomer configuration. The method has advantages of mild reaction conditions, easy separation and high stereospecificity of the products.

关 键 词：相转移催化法 1—O-芳酰基-2 3 4 6-四-O-乙酰基-β-D-吡喃己糖 杂环羧酸 糖苷键 

分 类 号：O626[理学—有机化学]