TRIFLIC ANHYDRIDE - AN ALTERNATIVE PROMOTER IN GLYCOSIDATIONS

被引:17
作者
DOBARRORODRIGUEZ, A [1 ]
TRUMTEL, M [1 ]
WESSEL, HP [1 ]
机构
[1] F HOFFMANN LA ROCHE & CO LTD,PRECLIN RES,DIV PHARM,CH-4002 BASEL,SWITZERLAND
关键词
D O I
10.1080/07328309208017992
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
The activation of glucosyl halides, trichloroacetimidates and of thioglucosides with triflic anhydride has been investigated showing that triflic anhydride promotes glycosidations with trichloracetimidates as well as with fluorides. There is also some potential for the activation of reactive thioglycosides. The role of triflic anhydride as a Lewis acid is likely.
引用
收藏
页码:255 / 263
页数:9
相关论文
共 39 条
[1]   2,3,4,6-TETRA-OMICRON-BENZYL-D-GLUCOSYL CHLORIDE + ITS USE IN SYNTHESIS OF ALPHA- + BETA-ANOMERS OF 2-OMICRON-D-GLUCOSYLGLYCEROL + 4-OMICRON-D-GLUCOSYL-D-RIBITOL [J].
AUSTIN, PW ;
BUCHANAN, JG ;
HARDY, FE ;
BADDILEY, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :2128-&
[2]   USE OF SULFENYL HALIDES IN CARBOHYDRATE REACTIONS .2. USE OF THE METHYLSULFENYL CATION AS AN ACTIVATOR FOR GLYCOSYLATION REACTIONS WITH ALKYL (ARYL) 1-THIOGLYCOPYRANOSIDES - SYNTHESIS OF METHYL O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]6)-O-ALPHA-D-GLUCOPYRANOSYL-(1-]2)-ALPHA-D-GLUCOPYRANOSIDE, A DERIVATIVE OF THE CORE TRISACCHARIDE OF ESCHERICHIA-COLI K12 [J].
DASGUPTA, F ;
GAREGG, PJ .
CARBOHYDRATE RESEARCH, 1990, 202 :225-238
[3]   SYNTHESIS OF 1,2-TRANS-RELATED 1-THIOGLYCOSIDE ESTERS [J].
FERRIER, RJ ;
FURNEAUX, RH .
CARBOHYDRATE RESEARCH, 1976, 52 (DEC) :63-68
[4]   DIRECT ELABORATION OF PENT-4-ENYL GLYCOSIDES INTO DISACCHARIDES [J].
FRASERREID, B ;
KONRADSSON, P ;
MOOTOO, DR ;
UDODONG, U .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (12) :823-825
[5]   A NOVEL, REDUCTIVE RING-OPENING OF CARBOHYDRATE BENZYLIDENE ACETALS, WITH UNUSUAL REGIOSELECTIVITY [J].
GAREGG, PJ ;
HULTBERG, H .
CARBOHYDRATE RESEARCH, 1981, 93 (01) :C10-C11
[6]  
HASHIMOTO S, 1990, TETRAHEDRON LETT, V31, P4769
[7]  
HASHIMOTO S, 1990, CHEM PHARM BULL, V38, P2323
[8]   GLYCOSYLATION USING GLUCOPYRANOSYL FLUORIDES AND SILICON-BASED CATALYSTS - SOLVENT DEPENDENCY OF THE STEREOSELECTION [J].
HASHIMOTO, S ;
HAYASHI, M ;
NOYORI, R .
TETRAHEDRON LETTERS, 1984, 25 (13) :1379-1382
[9]  
HASHIMOTO S, 1989, J CHEM SOC CHEM COMM, P865
[10]   GLUCOSYLATION USING GLUCOPYRANOSYL DIMETHYLPHOSPHINOTHIOATE [J].
INAZU, T ;
HOSOKAWA, H ;
SATOH, Y .
CHEMISTRY LETTERS, 1985, (03) :297-300