3-Azido-3-deoxy-glycopyranoside derivatives as scaffolds for the synthesis of carbohydrate-based universal pharmacophore mapping libraries.
The regiospecific syntheses of six monosaccharide scaffolds, 1-6, containing a carboxylic acid, an azido and a free hydroxyl group were accomplished through the utilization of a key intermediate, namely, methyl 3-azido-3-deoxy-beta-D-glucopyranoside (10). Scaffold 2 was also used in generating combinatorial libraries using solid-phase methodologies.
Jain
Rakesh
R
Intercardia Research Labs, 8 Cedar Brooke Drive, 08512, Cranbury, NJ, USA.
Kamau
Muthoni
M
Wang
Chunguang
C
Ippolito
Robert
R
Wang
Huiming
H
Dulina
Richard
R
Anderson
Jan
J
Gange
David
D
Sofia
Michael J
MJ
D001386:Azides / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002853:Chromatography, Liquid; D020650:Combinatorial Chemistry Techniques; D005449:Fluorenes / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D006900:Hydroxylation; D007202:Indicators and Reagents; D008027:Light; D013058:Mass Spectrometry; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012542:Scattering, Radiation
D001386:Azides; D002264:Carboxylic Acids; D005449:Fluorenes; D006027:Glycosides; D007202:Indicators and Reagents; D009005:Monosaccharides; C054007:1-(9-fluorenyl)methyl chloroformate