Abstract
AbstractA series of glycosyl serines 1–6 which are located in the carbohydrate‐protein linkage region of proteoglycans, including the chondrottin penta‐ and heptasaccharides GalNAcα(1–4)R (3), GalNAcß(1–4)R (4) and GalNAcß(1–4)GlcAß(1–3)GalNAc(1–4)R (6) as well as the heparin pentasaccharide GlcNAcα(1–4)R (5) [R = GlcAß(1–3)Galß(1–3)Galß(1–4)Xylß‐Ser] were systematically synthesized as follows. Trisaccharide acceptor 27 having a Gal(1–3)Galß(1–4)Xyl sequence was glycosylated with di‐ and tetrasaccharide donors 16α, 16ß, 22, and 26, which correspond to the non‐reducing end sequences of 3–6, regio‐ and stereoselectively to afford penta‐ and heptasaccharides 30, 34, 36, and 39, respectively. After the conversion into the respective penta‐ and heptaosylimidates 42c‐f as well as tri‐ and tetraosylimidates 42a and b, they were coupled with serine derivative 43 to give tri‐, tetra‐, penta‐, and heptaosyl serines 44a‐f. All the glycosyl serines were deprotected to 1–6.
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