Synthesis of 3-(beta-D-ribofuranosyl)-2-fluoropyridine and 3-(beta-D-ribofuranosyl)-pyridin-2-one

被引:27
作者
MatulicAdamic, J
Beigelman, L
机构
[1] Department of Organic Chemistry, Ribozyme Pharmaceuticals Inc., Boulder, CO 80301
关键词
D O I
10.1016/S0040-4039(96)02289-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyridin-2-one C-nucleoside 13 was prepared in 7 steps from 2-fluoropyridine 1 and D-ribono-1,4-lactone 2. The successful approach to beta-ribofuranosides 12 and 13 consisted of the reductive opening of the furanose ring of hemiacetal 3 followed by intramolecular Mitsunobu cyclization. Copyright (C) 1996 Elsevier Science Ltd
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页码:203 / 206
页数:4
相关论文
共 21 条
[1]   A CONVENIENT SYNTHESIS OF S-CYANOETHYL-PROTECTED 4-THIOURIDINE AND ITS INCORPORATION INTO OLIGORIBONUCLEOTIDES [J].
ADAMS, CJ ;
MURRAY, JB ;
ARNOLD, JRP ;
STOCKLEY, PG .
TETRAHEDRON LETTERS, 1994, 35 (05) :765-768
[2]   SYNTHESIS AND BIOLOGICAL EVALUATION OF A SERIES OF SUBSTITUTED PYRIDINE-C-NUCLEOSIDES .5. 3-CHLORO-4-(D-RIBOFURANOSYL)PYRIDINE AND 3-(D-RIBOFURANOSYL)-2-PYRIDONE [J].
BELMANS, M ;
VRIJENS, I ;
ESMANS, EL ;
DOMMISSE, RA ;
LEPOIVRE, JA ;
ALDERWEIRELDT, FC ;
TOWNSEND, LB ;
WOTRING, LL ;
BALZARINI, J ;
DECLERCQ, E .
NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (03) :307-315
[3]  
BURGIN AB, 1996, IN PRESS BIOCHEMISTR
[4]   THIAZOLE-BASED SYNTHESIS OF FORMYL C-GLYCOSIDES [J].
DONDONI, A ;
SCHERRMANN, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6404-6412
[5]   CHIRAL OXABICYCLIC SYSTEMS FROM RIBONOLACTONE [J].
DREW, MGB ;
MANN, J ;
THOMAS, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12) :2279-2285
[6]   The condensation of 2,6-dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation. [J].
Gudmundsson, KS ;
Drach, JC ;
Townsend, LB .
TETRAHEDRON LETTERS, 1996, 37 (14) :2365-2368
[7]   REGIOSELECTIVE METALATION IN A PYRIDINE SERIES - ORIGINAL SYNTHESIS OF 3-AROYL-2-AMINOPYRIDINES [J].
GUNGOR, T ;
MARSAIS, F ;
QUEGUINER, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 215 (02) :139-150
[8]  
HURUSAWA S, 1996, J ORG CHEM, V61, P4405
[9]  
Joos PE, 1996, HETEROCYCLES, V42, P173
[10]  
Joos PE, 1996, HETEROCYCLES, V43, P287