SYNTHESIS OF 2-CARBAMOYLMETHYL-6-BETA-D-RIBOFURANOSYLPYRIDINE WITH THE AID OF A PD(0)-CATALYZED REACTION

被引:12
作者
DEVOS, E [1 ]
ESMANS, EL [1 ]
ALDERWEIRELDT, FC [1 ]
BALZARINI, J [1 ]
DECLERCQ, E [1 ]
机构
[1] KATHOLIEKE UNIV LEUVEN,REGA INST MED RES,B-3000 LOUVAIN,BELGIUM
关键词
D O I
10.1002/jhet.5570300513
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
D-Allo/D-altro-2-(2,4:3,5-di-O-benzylidenepentitol-1-yl)-6-ethoxycarbonylmethylpyridine was synthesized from 2-bromo-6-(2,4:3,5-di-O-benzylidenepentitol-1-yl)pyridine or 2-(2,4:3,5-di-O-benzylidenepentitol-1-yl)-6-iodopyridine by means of a tetrakis(triphenylphosphine)palladium(0)-catalyzed reaction with Reformatsky's reagent. Subsequent ammonolysis and mesylation of the D-altro-ethoxycarbonylmethyl compound gave D-altro-2-carbamoylmethyl-6-(1-O-mesyl-2,4:3,5-di-O-benzylidenepentitol-1-yl)pyridine which was cyclized to 2-carbamoylmethyl-6-beta-D-ribofuranoslpyridine.
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收藏
页码:1245 / 1252
页数:8
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