NEW HIGHLY REGIOSELECTIVE REACTIONS OF UNPROTECTED SUCROSE - SYNTHESIS OF 2-O-ACYLSUCROSES AND 2-O-(N-ALKYLCARBAMOYL)SUCROSES

被引:61
作者
CHAUVIN, C [1 ]
BACZKO, K [1 ]
PLUSQUELLEC, D [1 ]
机构
[1] ENSCR,DEPT CHIM ORGAN,SYNTHESES & ACTIVAT BIOMOLECULES LAB,CNRS,URA D1467,AVE GEN LECLERC,F-35700 RENNES,FRANCE
关键词
D O I
10.1021/jo00060a053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New methodologies which lead selectively to chosen regioisomeric mono-O-acylsucroses are described. The results indicate that a selective ionization of the free sugar makes the secondary 2-OH group of the glucose moiety more nucleophilic than the primary hydroxyls. New 2-O-acylsucroses 2 and 2-O-(N-alkylcarbamoyl)sucroses 3 were thus obtained in high yields.
引用
收藏
页码:2291 / 2295
页数:5
相关论文
共 44 条
[1]   ON SOME PHYSICOCHEMICAL PROPERTIES OF SUCROSE ESTERS AND THE STABILITY THEY CONFER TO MEMBRANE-PROTEINS [J].
ABRAN, D ;
BOUCHER, F ;
HAMANAKA, T ;
HIRAKI, K ;
KITO, Y ;
KOYAMA, K ;
LEBLANC, RM ;
MACHIDA, H ;
MUNGER, G ;
SEIDOU, M ;
TESSIER, M .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 1989, 128 (01) :230-236
[2]  
ALLEN CFH, 1955, ORGANIC SYNTHESES CO, V3, P846
[3]   SUGAR CHEMISTRY WITHOUT PROTECTING GROUPS-III - A FACILE CHEMICAL SYNTHESIS OF 6-O-ACYL-D-GLYCOPYRANOSES AND METHYL-6-O-ACYL-D-GLYCOPYRANOSIDES [J].
BACZKO, K ;
PLUSQUELLEC, D .
TETRAHEDRON, 1991, 47 (23) :3817-3828
[4]   THE CONFORMATIONAL PROPERTIES OF SUCROSE IN AQUEOUS-SOLUTION - INTRAMOLECULAR HYDROGEN-BONDING [J].
BOCK, K ;
LEMIEUX, RU .
CARBOHYDRATE RESEARCH, 1982, 100 (MAR) :63-74
[5]   SUCROSE POLYESTER (SPE) - A NONCALORIC FAT [J].
BOGGS, RW .
FETTE SEIFEN ANSTRICHMITTEL, 1986, 88 (04) :154-158
[6]  
BOTTLE S, 1984, J CHEM SOC CHEM COMM, P385, DOI 10.1039/c39840000385
[7]  
BOX VGS, 1983, HETEROCYCLES, V20, P677
[8]   FURTHER REFINEMENT OF STRUCTURE OF SUCROSE BASED ON NEUTRON-DIFFRACTION DATA [J].
BROWN, GM ;
LEVY, HA .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1973, B 29 (APR15) :790-797
[9]   ENZYMATIC-SYNTHESIS OF VARIOUS 1'-O-SUCROSE AND 1-O-FRUCTOSE ESTERS [J].
CARREA, G ;
RIVA, S ;
SECUNDO, F ;
DANIELI, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :1057-1061
[10]  
CHAUVIN C, 1991, TETRAHEDRON LETT, V31, P3498