Guisheng Zhang, Jie Chen, J. Min
Jun 1, 2003
Citations
0
Influential Citations
6
Citations
Journal
Helvetica Chimica Acta
Abstract
The 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-β-D-mannopyranose (4) or the mixture of 1,3,6-tri-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-mannopyranose (10) and the corresponding α-D-glucopyranose-type glycosyl donor 9/10 reacted at room temperature with protected nucleosides 12–15 in CH2Cl2 solution in the presence of BF3⋅OEt2 as promoter to give 5′-O-(2-azido-2-deoxy-α-D-glycosyl)nucleosides in reasonable yields (Schemes 2 and 3). Only the 5′-O-(α-D-mannopyranosyl)nucleosides were obtained. Compounds 21, 28, 30, and 31 showed growth inhibition of HeLa cells and hepatoma Bel-7402 cells at a concentration of 10 μMin vitro.