One-pot synthesis of glucosamine oligosaccharides.
[reaction: see text] Tuning the reactivity of glycosyl donors derived from 2-amino-2-deoxy glucose by selective introduction of different N-protecting (NPhth and NHTroc) and anomeric leaving groups (ethylthio and phenylthio) enabled highly efficient oligosaccharide synthesis in a one-pot manner. One-pot sequential glycosylation of three and four units of 2-amino-2-deoxy glucose gave trisaccharides and tetrasaccharide in 50-81% yields.
Fridman
Micha
M
Department of Chemistry and Institute of Catalysis Science and Technology, Technion-Israel Institute of Technology, Haifa 32000, Israel.
Solomon
Dmitry
D
Yogev
Shay
S
Baasov
Timor
T
D005944:Glucosamine / Q000138:chemical synthesis* / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000737:chemistry
D009844:Oligosaccharides; D013865:Thioglycosides; D005944:Glucosamine