403616-60-4Relevant academic research and scientific papers
Complex structures of antennary human milk oligosaccharides - Synthesis of a branched octasaccharide
Knuhr, Petra,Castro-Palomino, Julio,Grathwohl, Matthias,Schmidt, Richard R.
, p. 4239 - 4246 (2007/10/03)
We have developed a highly convergent synthetic route for the synthesis of the branched structure of human milk octasaccharide β-D-galactopyranosyl-(1→3)-2-acetamido-2-de oxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl)- (1→4)-2-acetamido-2-deoxy-βD-glucopyranosyl-(1→6)-[β- Dgalactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-Dglucopyranosyl- (1→3)]-β-D-galactopyranosyl-(1→4)-α,β- Dglucopyranose (1). In the retrosynthetic analysis, target structure 1 was disconnected into building blocks 2-6. Starting from only four known building blocks - 4, 7, 8, and 12 - the required three disaccharide units were obtained, resulting after further protecting group manipulation and glycoside bond formation in the desired tetrasaccharides 13 and 16. Cleavage of the TBDMS group of 13 afforded tetrasaccharide 14, which was transformed into isolactosamine-β-(1→3)-lactosamine trichloroacetimidate 15. Removal of the 4b,6b-Obenzylidene group of tetrasaccharide 16 gave the lacto-Ntetraose acceptor 17, to afford the protected octasaccharide 18 on glycosylation with donor 15. Complete deprotection of the octasaccharide by way of 19 afforded target human milk oligosaccharide 1 in a short and efficient route.
