Synthesis of 2′-C-methyl-branched isonucleosides

被引:11
作者
Bouisset, Tony [1 ]
Gosselin, Gilles [1 ]
Griffe, Ludovic [1 ]
Meillon, Jean-Christophe [1 ]
Storer, Richard [1 ]
机构
[1] Lab Chim Med Idenix, F-34189 Montpellier 4, France
关键词
nucleoside analogues; isonucleosides; Valopicitabine; hepatitis C; anti-virals;
D O I
10.1016/j.tet.2008.05.022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel regioisomers of 2'-methyl-branched nucleosides were designed and synthesized to mimic potent anti-viral drugs like Valopicitabine. The short and efficient synthesis of the targets involves a one-pot tosylation/cyclization step that leads to an activated furan scaffold on which the isonucleosides were built. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6657 / 6661
页数:5
相关论文
共 29 条
[1]   Stereoselective synthesis of L-isonucleosides [J].
Aragonès, S ;
Bravo, F ;
Díaz, Y ;
Matheu, MI ;
Castillón, S .
TETRAHEDRON LETTERS, 2003, 44 (19) :3771-3773
[2]   NEW SYNTHESES OF 2'-C-METHYLNUCLEOSIDES STARTING FROM D-GLUCOSE AND D-RIBOSE [J].
BEIGELMAN, LN ;
ERMOLINSKY, BS ;
GURSKAYA, GV ;
TSAPKINA, EN ;
KARPEISKY, MY ;
MIKHAILOV, SN .
CARBOHYDRATE RESEARCH, 1987, 166 (02) :219-232
[3]  
Benzaria Samira, 2007, Antiviral Chemistry & Chemotherapy, V18, P225
[4]   A new general synthesis of isomeric nucleosides [J].
Bera, S ;
Nair, V .
TETRAHEDRON LETTERS, 2001, 42 (34) :5813-5815
[5]   SHORT CONVERGENT ROUTE TO HOMOCHIRAL CARBOCYCLIC 2'-DEOXYNUCLEOSIDES AND CARBOCYCLIC RIBONUCLEOSIDES [J].
BIGGADIKE, K ;
BORTHWICK, AD ;
EXALL, AM ;
KIRK, BE ;
ROBERTS, SM ;
YOUDS, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (14) :1083-1084
[6]   Stereoselective synthesis of both enantiomers of 1,4-anhydro-alditols, 1,4-anhydro-2-amino-alditols and D- and L-isonucleosides from 2,3-O-isopropylidene-D-glyceraldehyde using iodine-induced cyclization as the key step [J].
Bravo, F ;
Díaz, Y ;
Castillón, S .
TETRAHEDRON-ASYMMETRY, 2001, 12 (11) :1635-1643
[7]  
CAREY FA, 1990, ADV ORG CHEM, VA, P157
[8]   Convenient synthesis of nucleoside and isonucleoside analogues [J].
de Cienfuegos, LA ;
Mota, AJ ;
Robles, R .
ORGANIC LETTERS, 2005, 7 (11) :2161-2164
[9]   Synthesis of purine and pyrimidine isodideoxynucleosides from (S)-glycydol using iodoetherification as key step.: Synthesis of (S,S)-iso-ddA [J].
Díaz, Y ;
Bravo, F ;
Castillón, S .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17) :6508-6511
[10]   Structure-activity relationship of heterobase-modified 2′-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication [J].
Eldrup, AB ;
Prhavc, M ;
Brooks, J ;
Bhat, B ;
Prakash, TP ;
Song, QL ;
Bera, S ;
Bhat, N ;
Dande, P ;
Cook, PD ;
Bennett, CF ;
Carroll, SS ;
Ball, RG ;
Bosserman, M ;
Burlein, C ;
Colwell, LF ;
Fay, JF ;
Flores, OA ;
Getty, K ;
LaFemina, RL ;
Leone, J ;
MacCoss, M ;
McMasters, DR ;
Tomassini, JE ;
Von Langen, D ;
Wolanski, B ;
Olsen, DB .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (21) :5284-5297