蔗糖衍生物的合成及催化反应工艺
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摘要
为开辟新的蔗糖市场,系统地开展了可再生资源蔗糖的化学利用。在各种催化体系中对蔗糖及其衍生物三氯蔗糖和果糖深加工制备系列化合物,研究了产品性能及催化反应工艺。
NH2S03H-SiO2催化糖类全乙酰化反应,产率高于90.0%。全乙酰化产物具有α-型选择性,催化剂重复利用七次,五乙酰葡萄糖产率仍高达93.8%。
应用2-噻唑硫酮、苯并三唑和N-羟基苯并三唑为离去基团的活性酰化试剂合成了三氯蔗糖的关键中间体蔗糖-6-乙酸酯和蔗糖-6-丙酸酯,最高产率分别为73.1%和62.9%。CoCl2催化蔗糖与酸酐反应,以60.0%左右的产率选择性地制得天然产物3’-O-(4-甲氧苯甲酰基)蔗糖及其类似物。
考察微波辐射下质子酸、配合物和金属盐催化葡萄糖脱水转化为5-羟甲基糠醛(HMF)的产率,筛选出高效催化剂ZnCl2。300 W微波辐射8 mmin,葡萄糖、果糖和蔗糖为原料HMF产率分别为54.6%、55.1%和80.6%,在油浴加热条件0.11 g/mL糖溶液,ZnCl2/糖质量比1/4,189℃反应60 min,以葡萄糖、果糖和蔗糖为原料HMF产率分别为37.7%、42.7%和57.7%。微波辐射对催化糖降解合成HMF有明显促进作用,以蔗糖为原料HMF产率高于使用葡萄糖和果糖。比较了三种大批量制备HMF的方法,其中MgCl2·6H2O催化蔗糖首先降解为5-氯甲基糠醛、再水解羟基制备HMF的路线,操作简单、产物分离方便。
三氯蔗糖经两条路线分别制得新化合物1,6-二氯-1,6-二脱氧-2,3-O-异丙叉-β-D-呋喃果糖,产率为88.1%。以其为原料,经氯磺酰化、氨解合成含卤素原子的呋喃环构型氨基磺酸酯化合物,总产率47.4%。发现1,6-二氯-1,6-脱氧-2,3-O-异丙叉-β-D-呋喃果糖中基团离去活性由高到低为：Cl-6>OMs-4,C1-1。合成了两种未见报道的化合物6-0-苯甲酰基和6-叠氮-6-脱氧衍生物。以果糖为原料合成了托吡酯,三步反应总产率为42.3%,对托吡酯选择性水解异丙叉保护基、烷基化制备了N,N,O,O-四-乙基、N,N,O,O-四-丁基两种新的化学修饰物。
以2,3：45-二-O-异丙叉-β-D-吡喃果糖为原料,经对甲苯磺酰化、选择性水解、分子内醚化、氧化,合成了桥环手性酮1,5-脱水-2,3-O-异丙叉-β-D-吡喃果糖-4-酮,总产率23.5%。它催化(E)-肉桂醇的不对称环氧化,产率和ee值分别为58.5%和17.7%,它催化1-O叔丁基二甲基硅基-(E)-肉桂醇的不对称环氧化,产率和ee值分别为4.9%和95.7%。
The chemical untilization of renewable resource sucrose was improved in order to develop its new market. With sucrose and its derivatives suralose and fructose as raw materials, a series of compounds were synthesized in various catalytic systems. Technology of the catalytic process and properties of the products were studied.
Using supported catalyst NH2SO3H-SiO2, peracetylated saccharides were manufactured in the yields of more than 90.0%. The structure of products was focused onα- isomer. Even after the catalyst was recovered seven times, the yield of penta-O-acetylglucose was 93.8%.
The active reagents with 2-thiazolidinethione, benzotriazole and N-hydroxyl-benzotriazole as leaving groups reacted with sucrose, and then sucrose-6-actate and sucrose-6-propanoate were obtained in the highest yield of 73.1% and 62.9% respectively. Under the cocatalyst CoCl2, sucrose reacted with anhydride regioselectively giving the natural product 3'-O-(4-methoxybenzoyl)sucrose and its analogues in approximate 60.0% yield.
The catalytic effects of protonic acid, metal complex and salt were reviewed separately for the conversion of glucose into 5-hydroxymethylfurfural (HMF) assisted by microwave irradiation. Use of ZnCl2 gave the highest yield than all other catalytic systems. Under the conditions of microwave irradiation (300 W,8 min), HMF yields were 54.6%,55.1% and 80.6% from glucose, fructose and sucrose. Whereas upon conventional oil bath heating (0.11 g/mL sugar solution, weight ratio of ZnCl2 to substrate 1/4,189℃,60 min), HMF yields from glucose, fructose and sucrose were only up to 37.7%,42.7% and 57.7% respectively. Three large scale methods to manufacture FMF were studied. One method of them was that sucrose was converted to 5-chloromethylfurfural (CMF) firstly with MgCl2·6H2O as catalyst, then CMF was hydrolyzed to HMF. This method had the advantages of simple operation and convenient separation.
In the system of H2SO4/acetone, 1,6-dichloro-1,6-dideoxy-2,3-O-isopropylidene-β-D-fructofuranose was synthesized conveniently from sucralose in the yield of 88.1% for the first time. After chlorosulfonation and aminolysis, the furan sulfamate containg chlorine atoms was produced with a total yield 47.4%. It was indicated that the leaving activity of several groups was Cl-6>OMs-4,Cl-1. The new compounds of 6-O-benzoyl and 6-azido-6-deoxy were also synthesized. From fructose topiramate was manufactured via three steps in the total yield of 42.3%. After regioselective hydrolysis of the isopropylidene groups in topiramate and alkylation. two new compounds N,N,O,O-tetra-ethyl and N,N,O,O-tetra-butyl derivatives were obtained.
1,5-Anhydro-2,3-O-isopropylidene-β-D-fructopyranose-4-ketone was sythesized from 2,3:4,5-di-O-isopropylidene-(3-D-fructopyranose through tosylation, selective hydrolysis, intramolecular etherification and oxidation sequentially. The total yield was 23.5%. With this chiral ketone as catalyst of asymmetric epoxidation, the yield and ee value were 58.5% and 17.7% using (E)-cinnamyl alcohol as substrate. The yield and ee value were 4.9% and 95.7% using 1-O-TBS-(E)-cinnamyl alcohol as substrate.
NH2S03H-SiO2催化糖类全乙酰化反应,产率高于90.0%。全乙酰化产物具有α-型选择性,催化剂重复利用七次,五乙酰葡萄糖产率仍高达93.8%。
应用2-噻唑硫酮、苯并三唑和N-羟基苯并三唑为离去基团的活性酰化试剂合成了三氯蔗糖的关键中间体蔗糖-6-乙酸酯和蔗糖-6-丙酸酯,最高产率分别为73.1%和62.9%。CoCl2催化蔗糖与酸酐反应,以60.0%左右的产率选择性地制得天然产物3’-O-(4-甲氧苯甲酰基)蔗糖及其类似物。
考察微波辐射下质子酸、配合物和金属盐催化葡萄糖脱水转化为5-羟甲基糠醛(HMF)的产率,筛选出高效催化剂ZnCl2。300 W微波辐射8 mmin,葡萄糖、果糖和蔗糖为原料HMF产率分别为54.6%、55.1%和80.6%,在油浴加热条件0.11 g/mL糖溶液,ZnCl2/糖质量比1/4,189℃反应60 min,以葡萄糖、果糖和蔗糖为原料HMF产率分别为37.7%、42.7%和57.7%。微波辐射对催化糖降解合成HMF有明显促进作用,以蔗糖为原料HMF产率高于使用葡萄糖和果糖。比较了三种大批量制备HMF的方法,其中MgCl2·6H2O催化蔗糖首先降解为5-氯甲基糠醛、再水解羟基制备HMF的路线,操作简单、产物分离方便。
三氯蔗糖经两条路线分别制得新化合物1,6-二氯-1,6-二脱氧-2,3-O-异丙叉-β-D-呋喃果糖,产率为88.1%。以其为原料,经氯磺酰化、氨解合成含卤素原子的呋喃环构型氨基磺酸酯化合物,总产率47.4%。发现1,6-二氯-1,6-脱氧-2,3-O-异丙叉-β-D-呋喃果糖中基团离去活性由高到低为：Cl-6>OMs-4,C1-1。合成了两种未见报道的化合物6-0-苯甲酰基和6-叠氮-6-脱氧衍生物。以果糖为原料合成了托吡酯,三步反应总产率为42.3%,对托吡酯选择性水解异丙叉保护基、烷基化制备了N,N,O,O-四-乙基、N,N,O,O-四-丁基两种新的化学修饰物。
以2,3：45-二-O-异丙叉-β-D-吡喃果糖为原料,经对甲苯磺酰化、选择性水解、分子内醚化、氧化,合成了桥环手性酮1,5-脱水-2,3-O-异丙叉-β-D-吡喃果糖-4-酮,总产率23.5%。它催化(E)-肉桂醇的不对称环氧化,产率和ee值分别为58.5%和17.7%,它催化1-O叔丁基二甲基硅基-(E)-肉桂醇的不对称环氧化,产率和ee值分别为4.9%和95.7%。
The chemical untilization of renewable resource sucrose was improved in order to develop its new market. With sucrose and its derivatives suralose and fructose as raw materials, a series of compounds were synthesized in various catalytic systems. Technology of the catalytic process and properties of the products were studied.
Using supported catalyst NH2SO3H-SiO2, peracetylated saccharides were manufactured in the yields of more than 90.0%. The structure of products was focused onα- isomer. Even after the catalyst was recovered seven times, the yield of penta-O-acetylglucose was 93.8%.
The active reagents with 2-thiazolidinethione, benzotriazole and N-hydroxyl-benzotriazole as leaving groups reacted with sucrose, and then sucrose-6-actate and sucrose-6-propanoate were obtained in the highest yield of 73.1% and 62.9% respectively. Under the cocatalyst CoCl2, sucrose reacted with anhydride regioselectively giving the natural product 3'-O-(4-methoxybenzoyl)sucrose and its analogues in approximate 60.0% yield.
The catalytic effects of protonic acid, metal complex and salt were reviewed separately for the conversion of glucose into 5-hydroxymethylfurfural (HMF) assisted by microwave irradiation. Use of ZnCl2 gave the highest yield than all other catalytic systems. Under the conditions of microwave irradiation (300 W,8 min), HMF yields were 54.6%,55.1% and 80.6% from glucose, fructose and sucrose. Whereas upon conventional oil bath heating (0.11 g/mL sugar solution, weight ratio of ZnCl2 to substrate 1/4,189℃,60 min), HMF yields from glucose, fructose and sucrose were only up to 37.7%,42.7% and 57.7% respectively. Three large scale methods to manufacture FMF were studied. One method of them was that sucrose was converted to 5-chloromethylfurfural (CMF) firstly with MgCl2·6H2O as catalyst, then CMF was hydrolyzed to HMF. This method had the advantages of simple operation and convenient separation.
In the system of H2SO4/acetone, 1,6-dichloro-1,6-dideoxy-2,3-O-isopropylidene-β-D-fructofuranose was synthesized conveniently from sucralose in the yield of 88.1% for the first time. After chlorosulfonation and aminolysis, the furan sulfamate containg chlorine atoms was produced with a total yield 47.4%. It was indicated that the leaving activity of several groups was Cl-6>OMs-4,Cl-1. The new compounds of 6-O-benzoyl and 6-azido-6-deoxy were also synthesized. From fructose topiramate was manufactured via three steps in the total yield of 42.3%. After regioselective hydrolysis of the isopropylidene groups in topiramate and alkylation. two new compounds N,N,O,O-tetra-ethyl and N,N,O,O-tetra-butyl derivatives were obtained.
1,5-Anhydro-2,3-O-isopropylidene-β-D-fructopyranose-4-ketone was sythesized from 2,3:4,5-di-O-isopropylidene-(3-D-fructopyranose through tosylation, selective hydrolysis, intramolecular etherification and oxidation sequentially. The total yield was 23.5%. With this chiral ketone as catalyst of asymmetric epoxidation, the yield and ee value were 58.5% and 17.7% using (E)-cinnamyl alcohol as substrate. The yield and ee value were 4.9% and 95.7% using 1-O-TBS-(E)-cinnamyl alcohol as substrate.
引文
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