Coupling of 2,6-disubstituted purines to ribose-modified sugars.
1,2,3-Tri-O-acetyl-N-ethyl-beta-D-ribofuranuronamide was synthesized in three steps starting from 1-O-methyl-(2,3-O-isopropylidene)-beta-D-ribofuranuronic acid. Both the triacetyl and the 1-O-methyl-2,3-di-O-acetyl derivatives were coupled to the 2,6-dichloropurine to obtain the acetylated 1-(2,6-dichloro-9H- purin-9-yl)-1-deoxy-N-ethyl-beta-D-erythro-pentofuranuronamide. 1H NMR and n.O.e. data accounted for both anomeric and N-7/N-9 isomeric configuration.
Vittori
S
S
Dipartimento di Scienze Chimiche, via s. Agostino, 1, University of Camerino, I-62032 Camerino, Italy.
Costanzi
S
S
Lambertucci
C
C
Volpini
R
R
Cristalli
G
G
D008024:Ligands; D009005:Monosaccharides / Q000138:chemical synthesis*; D011687:Purines / Q000138:chemical synthesis*; D018047:Receptors, Purinergic P1 / Q000378:metabolism; D012266:Ribose / Q000031:analogs & derivatives*
C442709:1,2,3-tri-O-acetyl-N-ethyl-ribofuranuronamide; D008024:Ligands; D009005:Monosaccharides; D011687:Purines; D018047:Receptors, Purinergic P1; D012266:Ribose