APPLICATION OF A PHASE-TRANSFER REACTION TO THE SYNTHESIS OF L-FRUCTOSE

被引：15

作者：

GIZAW, Y

BEMILLER, JN

机构：

[1] PURDUE UNIV,DEPT FOOD SCI,W LAFAYETTE,IN 47907

[2] PURDUE UNIV,WHISTLER CTR CARBOHYDRATE RES,W LAFAYETTE,IN 47907

来源：

CARBOHYDRATE RESEARCH | 1995年 / 266卷 / 01期

关键词：

PHASE TRANSFER CATALYSIS; SYNTHESIS OF L-FRUCTOSE; FRUCTOSE; L-;

D O I：

10.1016/0008-6215(94)00255-E

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-alpha-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O- (p-tolylsulfonyl)-alpha-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-alpha-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).

引用

页码：81 / 85

页数：5

共 25 条

[1] CYCLIC ACETALS OF KETOSES .3. RE-INVESTIGATION OF SYNTHESIS OF ISOMERIC DI-0-ISOPROPYLIDENE-BETA-D-FRUCTOPYRANOSES [J].