Synthesis of glycan fragments of glycoproteins using peracetylated N-allyloxycarbonyl-β-D-glucosamine and 1,6-anhydro-β-D-mannopyranose derivatives

Abstract

. Can. J. Chem. 68, 828 (1990). The disaccharides P-~-GlcNAoC- (142) The anhydro glycosylation products obtained were then easily transformed into the 4~1 peracetylated derivatives by acetolysis. The N-allyloxycarbonyl groups could be converted into N-acetyl groups in the presence of Pd(0) complexes, followed by reacetylation of the free amino function in high yields.

Use of the p-nitrobenzyloxycarbonyl group as an orthogonal amine protecting group in the synthesis of β-GlcNAc terminating glycosides

“…The 2,2,2-trichloroethyl and allyl carbamates have since been effectively applied in the synthesis of glycoconjugates containing 2-acetamido glycosides. 7,9 These can be deprotected with zinc dust in acetic acid 7 and with Pd 0 complexes, 9 respectively.…”

Synthesis of a Branched Heptose- and Kdo-Containing Common Tetrasaccharide Core Structure of Haemophilus influenzae Lipopolysaccharides via a 1,6-Anhydro-l-glycero-β-d-manno-heptopyranose Intermediate

“…Another solution to this problem of steric crowding is to change completely the conformation of the hexose ring by forming a 1,6-anhydro bridge. , This will force the ring from a 4 C 1 to a 1 C 4 conformation, and consequently the equatorial O-3 and O-4 will become axial with possible steric release between 3- and 4-substituents. This approach was tried using the known 1,6-anhydro-β- d -mannose , as a precursor and model compound but also with the intention to make the target heptose saccharide by a one-carbon elongation at a later stage. The desired 3,4-branched structures could conveniently be prepared using this strategy, but when the elongation was attempted, problems were encountered already in the acetolysis of the anhydro bridge due to the protection group pattern used. , We therefore decided to try the same strategy but to start from a heptose derivative, thereby avoiding the later elongation.…”