摘要
研究了核糖的酰化、氯代合成工艺,并对其反应工艺进行了优化.首先以价廉的D-核糖为原料,先经过甲基化合成得到混合构型的1-甲氧基-D-核糖,接着与对氯苯甲酰氯反应得到1-甲氧基-2,3,5-三-氧-对氯苯甲酰基-D-核糖,再与乙酸酐在浓硫酸的催化下,乙酰化生成了1-乙酰氧基-2,3,5-三-氧-对氯苯甲酰基-D-呋喃核糖,最后在无水二氯甲烷中脱乙酰基得到最终产物1位氯代核糖.结果显示:1-乙酰氧基-2,3,5-三-氧-对苯甲酰基-D-呋喃核糖氯代后得到混合构型的粉末状氯代糖,收率达84.9%,经过三次重结晶得到β型的氯代糖,收率62.4%,产物的性状已经过红外和核磁鉴定.
The experiment studied the optimum condition of the protection and chlorination of D- ribose. D-ribose was first added in 1 mol/L anhydrous HCl/ MeOH solution to obtain 1-O- methyl-D-ribose, which then subsequently protected by p-nitrobenzoyl chloride to synthesis 1-O- methyl-2,3, 5-O-tris （4-chlorobenzoyl）-D-ribofuranose, further reacting with acetic anhydride under the catalysis of oil of vitriol to produce 1-O-acetyl-2,3,5-tri-O-（4-chlorobenzoyl）- beta-D- ribofuranose. Finally the product was treated with dry HCl gas in refluxing dichloromethane to obtain crystalline chloro ribose as a mixture solid of a and β form with a yield of 84.9%. After recrystallized three times, only β anomer was left in a yield of 62.4%. Structure of the product was identified by IR and ^1H NMR characterization.
出处
《浙江工业大学学报》
CAS
2013年第3期275-279,共5页
Journal of Zhejiang University of Technology
基金
浙江省重大专项项目(2009C13033-1)
关键词
D-核糖
氯代
结晶
D-ribose
chlorination
crystal
