19488-50-7

Upstream product

• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 280136-32-5 p-nitrophenyl 2,3,6-tri-O-acetyl-4-O-methyl-α-D-glucopyranoside 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 39131-44-7 5-bromomethyl-furan-2-carbaldehyde 
• 1917-65-3 5-(ethoxymethyl)furfural 

Relevant academic research and scientific papers

Synthesis of 5-bromomethylfurfural from cellulose as a potential intermediate for biofuel

Cellulose can be converted into 5-bromomethylfurfural (BMF), a brand new biofuel or biofuel intermediate, in 80 yield by treatment with HBr and LiBr and continuous extraction with toluene. From other carbohydrates and straw, BMF was also obtained in high yields. The mechanism of BMF formation was investigated, and the results indicate that this furfural is formed during the depolymerization of cellulose and that glucose is not an intermediate.

New method for regioselective glycosylation employing saccharide oxyanions

As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were used as a model system to study the underlying mechanistic principles of base-promoted glycosylation. High regioselectivities and stereospecific glycosidic bond formations were achieved, and the scope of the methodology was extended with different perbenzylated glycosyl donors.

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.