CONFORMATIONAL FLEXIBILITY OF C-GLYCOSIDES - EXPERIMENTAL-EVIDENCE OFTHE EXISTENCE OF A GAUCHE-GAUCHE CONFORMATION AROUND THE GLYCOSIDIC LINKAGE FOR A LACTOSE ANALOG

Authors
ESPINOSA JF DIETRICH HJ MARTINLOMAS M SCHMIDT RR JIMENEZBARBERO J
Citation
Jf. Espinosa et al., CONFORMATIONAL FLEXIBILITY OF C-GLYCOSIDES - EXPERIMENTAL-EVIDENCE OFTHE EXISTENCE OF A GAUCHE-GAUCHE CONFORMATION AROUND THE GLYCOSIDIC LINKAGE FOR A LACTOSE ANALOG, Tetrahedron letters, 37(9), 1996, pp. 1467-1470
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
9
Year of publication
1996
Pages
1467 - 1470
Database
ISI
SICI code
0040-4039(1996)37:9<1467:CFOC-E>2.0.ZU;2-R
Abstract
The solution conformation of C-glycosides 3 and 4, presenting a hydrox yl group at the bridging position, has been determined by NMR and MM3 calculations. The conformation of 3 is similar to that of C-lactose, while that of 4 is rather different and shows a significant contributi on of a conformer with a gauche disposition between C1'-05' and C1'-C2 ' bonds.