208758-71-8

Upstream product

• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 13242-53-0 acetobromomannose 
• 108-24-7 acetic anhydride 
• 96996-90-6 1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside 
• 108671-41-6 methyl 2,3,4-tri-O-benzyl-6-O-α-D-mannopyranosyl-α-D-mannopyranoside 

Downstream Products

• 108671-41-6 methyl 2,3,4-tri-O-benzyl-6-O-α-D-mannopyranosyl-α-D-mannopyranoside 
• 78962-39-7 methyl α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside 
• 72691-29-3 2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl-(1→6)-1,2,3,4-tetra-O-acetyl-α-D-mannopyranose 

Relevant academic research and scientific papers

Solvent-Free Glycosylation from per-O-Acylated Donors Catalyzed by Methanesulfonic Acid

The huge importance of carbohydrates and their derivatives in biomedical and industrial applications call for the development of streamlined and sustainable procedures for their synthetic elaboration. Here reported a novel glycosylation method based on direct activation of readily available per-O-acylated (acetylated or benzoylated) donors, promoted under air by methanesulfonic acid as a cheap and green catalyst in the absence of any solvent. Besides the beneficial avoidance of toxic and polluting organic solvents, these conditions were found critical for activating such poorly reactive donors with a very small catalyst loading (only 5 mol %), instead of stoichiometric Lewis acid promoters typically employed. Desired glycosides were quickly obtained, in most cases with high 1,2-trans stereoselectivity. Other main advantages over reported glycosylations with similar donors are the limited stoichiometric excess of the acceptor (or the donor), the easy applicability and low cost of the procedure and the wide target scope, also covering the synthesis of disaccharides and other non-trivial glycosides with applicable potential.

Radical halogenation-mediated latent-active glycosylations of allyl glycosides

Radical halogenation-mediated glycosylation using allyl glycosides as donors and as acceptors emerges to be an efficient and hither-to unknown glycosylation method, adhering to the concept of the latent-active methodology. Several di- and trisaccharides that possess the allyl moiety at their reducing end are prepared through this new glycosylation methodology.

Synthesis and semisynthesis of some structural elements of oligo-mannose type N-glycoproteins

For the construction of N-glycoprotein glycan chains, valuable potential glycosyl donors, O-α-D-mannopyranosyl-(1→2)-α-D-mannopyranose octaacetate (19) and O-α-D-mannopyranosyl-(1→2)-O-α-D-mannopyranosyl-(1→2)- α-D-mannopyranose undecaacetate (20) were ob

LYSOSOMAL-ENZYME TARGETING: THE PHOSPHORYLATION OF SYNTHETIC D-MANNOSYL SACCHARIDES BY UDP-N-ACETYLGLUCOSAMINE:LYSOSOMAL-ENZYME N-ACETYLGLUCOSAMINE-PHOSPHOTRANSFERASE FROM RAT-LIVER MICROSOMES AND FIBROBLASTS

Phosphorylation of the D-mannose residues of lysosomal-enzymes is essential for the uptake and intracellular transport of these enzymes to lysosomes.The GlcNAc-P-transferase which is involved in the phosphorylation reaction seems to recognize a signal, probably a protein conformation, common to many lysosomal enzymes.To evaluate the role of the carbohydrate portion of the enzyme in these phosphorylation reactions, the acceptor specificity of GlcNAc-P-transferase from rat-liver microsomes and fibroblasts was examined with the aid of synthetic D-mannosyl disaccharides and derivatives that are closely related to the high-mannose type of oligosaccharides.Four methyl D-mannobiosides were synthesized, and their structures were established by 13C-n.m.r. spectroscopy.Of all the D-mannosyl saccharides tested, α-D-Man-(1->2)-α-D-Man-(1->OMe) was found to be the best acceptor, thereby suggesting that oligosaccharide structure may also have a role to play in recognition by this enzyme.