酒石酸衍生物的合成及其结构与光学活性关系的探讨

Studies on the Relationship between the Structures of TartaricAcid Derivatives and Their Optical Activities

合成出系列的L 半螺旋型酒石酸衍生物 1～ 6 ,测定比旋光度 ,发现酒石酸二乙酯 2 ([α]2 5D+ 3 0 0° ,DMSO)形成 2 ,3 O 亚异丙基酒石酸二乙酯 3后旋光急剧往左偏移 ([α]2 5D - 4 5 0 3° ,DMSO) ,3酰胺化后比旋光值往右偏移 (4a :+ 11 19° ,4b :+ 2 14°) ,还原产物的比旋光值往左偏移 (5a :- 0 5 2° ,5b :- 4 92° ,6 :- 2 95°) ;

Several L-tartaric acid derivatives (1～6) were synthesized and their specific rotations were measured.It was found that diester 3 exhibited an unusually high negative value of specific rotation ([α] 25 D-45 03°,DMSO),its amide derivatives 4 showed slightly positive specific rotation (4a:+11^19°,4b:+2 14°),and the reduction products showed slightly negative values (5a:-0 52°,5b:-4 92°,6:-2 95°).The optical activities of 1～6 were elucidated by the polarization ability of functional groups and the helical structures.