109280-62-8

Basic information

• Product Name: methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside
• Synonyms: methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside
• CAS NO: 109280-62-8
• Molecular Weight: 386.445
• Mol File: 109280-62-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside(109280-62-8)
• EPA Substance Registry System: methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside(109280-62-8)

Safety Data

• Hazardous Substances Data: 109280-62-8(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 110715-29-2 methyl 4,6-O-benzylidene-2-O-methyl-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 110594-89-3 3,4,6-tri-O-acetyl-2-O-methyl-1-deoxy-1-piperidino-β-D-glucose 
• 2140-41-2 2-O-methyl-D-glucopyranose 
• 81024-47-7 methyl 2-O-methylglucopyraniside 

Downstream Products

• 57783-74-1 methyl 3,4-di-O-benzyl-2,6-di-O-methyl-α-D-glucopyranoside 
• 50705-62-9 methyl 3-O-benzyl-2-O-methyl-α-D-glucopyranoside 
• 110618-67-2 Methanesulfonic acid (2R,3R,4R,5R,6S)-4-benzyloxy-2-methanesulfonyloxymethyl-5,6-dimethoxy-tetrahydro-pyran-3-yl ester 
• 82160-01-8 methyl 3-O-benzyl-6-deoxy-2-O-methyl-D-arabino-hexopyranosid-4-ulose 
• 110594-91-7 methyl 3-O-benzyl-6-deoxy-2-O-methyl-α-D-ggalactopyranoside 
• 95058-34-7 methyl 3-O-benzyl-6-deoxy-2-O-methyl-α-D-glucopyranoside 
• 87256-58-4 3-O-benzyl-6-deoxy-2-O-methyl-D-galactose diethyldithioacetal 

Relevant articles and documents

Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity

Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.

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.