116296-68-5Relevant articles and documents
Anomeric acetates of N-acetylneuraminic acid are useful C-sialyl donors in samarium-mediated reformatsky coupling reactions
Malapelle, Adeline,Abdallah, Zouleika,Doisneau, Gilles,Beau, Jean-Marie
, p. 6016 - 6020 (2006)
(Chemical Equation Presented) Teaching an old molecule new tricks: A new solution for an expeditious C-sialylation from N-acetylneuraminic acid involves the use of the peracetylated derivative 1, a very common starting material prepared 40 years ago in He
SYNTHESE EINES N-ACETYLNEURAMINSAEURE-HALTIGEN SYNTHESEBLOCKS. KUPPLUNG ZUM N-ACETYLNEURAMINSAEURE-TETRASACCHARID MIT TRIMETHYLSILYLTRIFLAT
Paulsen, Hans,Tietz, Holger
, p. 205 - 230 (2007/10/02)
A trisaccharide synthetic block consisting of N-acetylneuraminic acid and lactosamine that allows general coupling reactions to other saccharide units was obtained.O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α- and -β-D-glycero-D-galacto-2-nonulopyranosylonate)-(2->6)-O-(2,3,4-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-1,3,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranose were used as glycosyl donors.In the presence of trimethylsilyltriflate, both compounds were converted into tetrasaccharides by reaction with derivatives of D-mannose unsubstituted at OH-2 representing the glycosyl acceptors.Removal of the protecting groups gave O-(5-acetamido-3,5-dideoxy-α- and -β-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-β-D-galactopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-D-mannopyranose, respectively.