108671-41-6

Upstream product

• 74808-17-6 Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester 
• 40653-30-3 methyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-galactopyranoside 
• 40653-32-5 methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 18311-26-7 methyl 6-O-triphenylmethyl-β-D-galactopyranoside 
• 208758-71-8 Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester 
• 96996-90-6 1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside 
• 1192366-15-6 C₆₂H₅₈O₁₅ 
• 13242-53-0 acetobromomannose 
• 100-39-0 benzyl bromide 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 208758-71-8 Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester 
• 78962-39-7 methyl α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside 

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.

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.

PREPARATION OF α AND Β ANOMERS OF VARIOUS ISOMERIC METHYL O-D-GALACTOPYRANOSYL-D-GALACTOPYRANOSIDES. STANDARDS FOR INTERPRETATION OF 13C-N.M.R. SPECTRA OF D-GALACTOPYRANANS

The four isomer of methyl O-β-D-galactopyranosyl-β-D-galactopyranoside were prepared by condensation of 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl bromide with appropriate, partially O-substitued derivatives of methyl β-D-galactopyranoside.Reaction of 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose with the same acceptors, in the presence of mercuric bromide, led to the formation of α and β linkages.Thus, it was possible to assign 13C-n.m.r. resonances of α and β anomers of methyl O-D-galactopyranosyl-β-D-galactopyranosides.In terms of application of these shift values and those of related D-galactobioses to the structual analysis of D-galactopyranans by shift comparisons, some generalizations can be made.For β-D-galactopyranans, the resonances glycosyloxylated carbon atoms of methyl O-β-D-galactopyranosyl-β-D-galactopyranosides are sensitive to structure and appear to have typical values, whereas limited variation was observed with shift of C-1' signals.On the other hand, for assigning structures to D-galactopyranans containing α linkages, the C-1' shifts (at higher field) of methyl O-α-D-galactopyranosyl-β-D-galactopyranosidesc are sensitive to linkage position, whereas those of glycosyloxylated carbon atoms vary only a little.