7468-45-3

Upstream product

• 67-56-1 methanol 
• 55058-41-8 O⁴-methyl-α-D-mannopyranose 
• 118895-71-9 1,6-anhydro-2,3-di-O-isopropylidene-4-O-methyl-β-D-mannopyranose 
• 186581-53-3 diazomethane 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 88110-51-4 methyl 2,3-di-O-benzyl-4-O-methyl-α-D-mannopyranoside 
• 7647-01-0 hydrogenchloride 
• 64043-86-3 D-manno-2,3,5,6-Tetrahydroxy-4-methoxy-hexanal 
• 280136-54-1 methyl 2,3,6-tri-O-benzyl-4-O-methyl-α-D-mannopyranoside 
• 19488-48-3 methyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside 
• 6988-40-5 methyl 2,3-di-O-benzyl-α-D-mannopyranoside 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 186540-01-2 ((2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-3,6-dimethoxy-tetrahydro-pyran-2-ylmethoxy)-tert-butyl-diphenyl-silane 
• 169396-75-2 (2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol 

Downstream Products

• 24707-29-7 2-O-Methyl-D-erythrit (3-O-Methyl-L-erythrit) 
• 58178-82-8 methyl-[O²,O³-diacetyl-O⁴-methyl-O⁶-(toluene-4-sulfonyl)-α-D-mannopyranoside] 

Relevant academic research and scientific papers

TMC-171A, B, C and TMC-154, novel polyketide antibiotics produced by Gliocladium sp. TC 1304 and TC 1282

Four new antibiotics, TMC-171A (2), B (3), C (4) and TMC-154 (5) have been isolated from the fermentation of fungal strains Gliocladium sp. TC 1304 and TC 1282, respectively. Spectroscopic and degradation studies have shown that TMC-171s and TMC-154 were new members of the TMC-151 class of antibiotics, unique polyketides modified with a D-mannose and a D-mannitol or a D-arabitol. These compounds showed moderate cytotoxicity to various tumor cell lines.

Synthesis of monomethyl derivatives of p-nitrophenyl α-d-gluco, galacto, and mannopyranosides and their hydrolytic properties against α-glycosidases

All possible monomethyl derivatives of p-nitrophenyl α-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of α-glucosidase (rice), α-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and α-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea α-galactosidase and the almond and jack bean α-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, rice α-glucosidase and green coffee bean and A. niger α-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

Analysis of the binding specificities of oligomannoside-binding proteins using methylated monosaccharides

The binding specificities of the closely related lectins from Canavalia ensiformis and Dioclea grandiflora were examined using specifically O-alkylated mono- and disaccharides. Both lectins accept any substitution at the monosaccharide C2 hydroxyl group. The binding energy of C2-alkylated ligands-concanavalin A complexes increases by 1 kcal mol-1 for the C2-O-ethyl ligand, while the binding energies of the corresponding complexes with the Dioclea lectin are identical. Both lectins accept methyl, but not ethyl, substitution of the C3 hydroxyl, in contrast to earlier reports. The results are interpreted in terms of existing models of the concanavalin A binding site. While the results are consistent with a model of the concanavalin A extended binding site that places the non-reducing terminus of all disaccharides in the monosaccharide binding site, they point to the dangers of interpreting the binding behavior of unnatural saccharide ligands on the basis of crystallographic data obtained with native ligands.

METHYLATION OF METHYL α-D-HEXOPYRANOSIDES WITH DIAZOMETHANE IN THE PRESENCE OF A SMALL AMOUNT OF WATER

The long-time reaction of methyl α-D-gluco-, α-D-manno-, and α-D-galactopyranosides with excess diazomethane-diethyl ether at 25 deg C the presence of water gave all partially methylated methyl α-D-hexopyranosides which differ in number and position of methyl substitution.The presence electrolytes, such as potassium or sodium phosphate, in the reaction medium enhanced the degree of methylation, resulting in preferential formation of tri-O-methyl derivatives of methyl α-D-hexopyranosides.