A versatile and stereocontrolled route to pyranose and furanose C-glycosides

被引:30
作者
Harvey, JE [1 ]
Raw, SA [1 ]
Taylor, RJK [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
D O I
10.1021/ol0490678
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.
引用
收藏
页码:2611 / 2614
页数:4
相关论文
共 33 条
[1]   Stereocontrolled synthesis of cyclic ethers by intramolecular hetero-Michael addition .5. Synthesis of all diastereoisomers of 2,3,5,6-tetrasubstituted tetrahydropyrans [J].
Betancort, JM ;
Martin, VS ;
Padron, JM ;
Palazon, JM ;
Ramirez, MA ;
Soler, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4570-4583
[2]   Carbohydrate mimetics-based glycosyltransferase inhibitors [J].
Compain, P ;
Martin, OR .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (12) :3077-3092
[3]   STEREOCONTROLLED ROUTES TO FUNCTIONALIZED C-GLYCOPYRANOSIDES [J].
DAWE, RD ;
FRASERREID, B .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :522-528
[4]   TOTAL SYNTHESIS OF ELFAMYCINS - AURODOX AND EFROTOMYCIN .1. STRATEGY AND CONSTRUCTION OF KEY INTERMEDIATES [J].
DOLLE, RE ;
NICOLAOU, KC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1691-1694
[5]  
Dondoni A, 2002, SYNLETT, P89
[6]   Methods for anomeric carbon-linked and fused sugar amino acid synthesis: The gateway to artificial glycopeptides [J].
Dondoni, A ;
Marra, A .
CHEMICAL REVIEWS, 2000, 100 (12) :4395-+
[7]   Recent advances in stereoselective C-glycoside synthesis [J].
Du, YG ;
Linhardt, RJ ;
Vlahov, IR .
TETRAHEDRON, 1998, 54 (34) :9913-9959
[9]   DIASTEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED C-ALPHA-GLYCOSYL DERIVATIVES AND C-BETA-GLYCOSYL DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-D-GLUCOSE [J].
GIANNIS, A ;
SANDHOFF, K .
CARBOHYDRATE RESEARCH, 1987, 171 :201-210
[10]   Studies of rhodium-catalyzed ring opening of vinyl epoxides [J].
Ha, JD ;
Shin, EY ;
Kang, SK ;
Ahn, JH ;
Choi, JK .
TETRAHEDRON LETTERS, 2004, 45 (21) :4193-4195