摘要
糖酯类化合物具有广泛的生理活性,如抗菌、抗肿瘤等。1987年Trivedi等首次使用苯甲酰基保护的溴化α-D-葡萄糖与桂皮酸类在相转移催化剂三甲基十六烷基溴化铵的存在下反应,合成了收率为53％～82％的糖酯,此结果与Inch的结果不一致。我们在前文的基础上用2,3,4,6-四-O-乙酰基-α-D-溴代吡喃葡萄糖(1)与桂皮酸类(2～5)及与苯甲酸类(10～16),在催化剂四丁基溴化铵的存在下反应,合成了糖酯(6～9,17～23),收率为58％～82％。产品具有高度的立体选择性,~1H NMR的化学位移δ值在5.89～6.01,偶合常数J:7.2～8.1Hz,1R光谱在902.2 cm^(-1)左右具有特征吸收峰,证实为β端基异构体。
2,3,4,6-Tetra-O-acetyl-α-D-glucosyl bromide reacts with carboxylic acids in the presence of phase transfer catalysts to give carbohydrate esters. There are many advantages in this method, such as good yields, mild reaction conditions and high stereospecificity. The results conclusively disproved a report by Inch and his co-workers that the phase-transfer method requires a nonparticipating group at C-2 or C-6 in the carbohydrate moiety.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
1991年第3期349-350,共2页
Chemical Journal of Chinese Universities
关键词
碳水化合物
相转移催化
糖酯
Phase-transfer catalysis, Carbohydrate ester, Tetrabutylammonium bromide
