Chiral O-(Z-alpha-aminoacyl) sugars: convenient building blocks for glycopeptide libraries.
1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose (2), 1,2:5,6-di-O-isopropylidene-d-glucose (5), and 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose (7) are efficiently O-acylated in 78-96% yields with readily available N-(Z-alpha-aminoacyl)benzotriazoles 1a-e, 1d+1d' under microwave irradiation to give chiral 3a-d, 4, 6a-d, 8a,b and diastereomeric mixtures (3d+3d'), (6a+6a'), and (6d+6d'). The original chirality was retained as evidenced by HPLC. The diisopropylidene protecting groups were removed from compounds 3a,d, 6d to give the free O-(Z-alpha-aminoacyl) sugars 9a,b, 10.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Angrish
Parul
P
Narindoshvili
Tamari
T
D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D006601:Hexoses / Q000138:chemical synthesis / Q000737:chemistry*; D019151:Peptide Library; D013237:Stereoisomerism
C522269:(3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl 2-((benzyloxy)carbonyl)amino-3-phenylpropanoate; D002219:Carbamates; D006020:Glycopeptides; D006601:Hexoses; D019151:Peptide Library