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A concise chemical synthesis of a series of structurally-defined heparin-like oligosaccharides is described. This work provides an efficient entry to octa-, deca-, and dodecasaccharides, including the first synthesis of (GlcNS6S-IdoA2S)5 and (GlcNS6S-IdoA2S)6. Evaluation of the in vitro activity of these species against FGF2- and VEGF165- dependent endothelial cell proliferation and migration establishes that octa- and decasaccharides are more potent in targeting FGF2-induced effects, where cell migration is affected more significantly than proliferation. These structure-activity relationships exemplify the significance of 6-O-sulfation in regulating the activity of angiogenic growth factors. © 2013 The Royal Society of Chemistry.