An efficient synthesis of triazolo-carbohydrate mimetics and their conformational analysis.
A chemical library of 1,2,3-triazole fused carbohydrate mimetics was constructed. To synthesize enantiomerically pure mimetics, we developed a stereo- or diastereodivergent synthetic route from D-glucose, D-mannose and D-galactose as chiral sources. In this synthesis, an In(OTf)(3)-catalyzed tandem azidation-1,3-dipolar cycloaddition reaction of 1,1-dimethoxyhex-5-yne derivatives with TMSN(3) was used as the key step to construct the 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine framework. Additionally, NMR was used to carry out a conformational analysis of the synthesized mimetics, which are of structural interest since they have an N,O-acetal moiety in place of the anomeric position of normal pyranosides.
Yanai
Hikaru
H
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Hachioji, Tokyo, Japan.
Obara
Shun
S
Taguchi
Takeo
T
D000480:Alkynes / Q000737:chemistry; D032701:Biomimetics; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D015394:Molecular Structure; D054852:Small Molecule Libraries; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D002241:Carbohydrates; D054852:Small Molecule Libraries; D014230:Triazoles