56586-54-0

Basic information

• Product Name: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside
• Synonyms: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside
• CAS NO: 56586-54-0
• Molecular Weight: 310.347
• Mol File: 56586-54-0.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside(56586-54-0)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside(56586-54-0)

Safety Data

• Hazardous Substances Data: 56586-54-0(Hazardous Substances Data)

Upstream product

• 120408-72-2 Methyl 2,3-anhydro-4,6-O-(phenylmethylene)-β-D-allopyranoside 
• 98-87-3 benzylidene dichloride 
• 10227-29-9 methyl 2,3-di-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 3396-99-4 methyl α-D-galactopyranoside 
• 6752-76-7 methyl 4,6-O-benzylidene-2-O-methyl-β-D-idopyranoside 
• 129831-96-5 methyl 4,6-O-(S)-benzylidene-3-O-methyl-β-D-idopyranoside 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 74560-62-6 methyl 4,6-O-(S)-benzylidene-2-methyl-α-D-idopyranoside 
• 74560-63-7 methyl 4,6-O-(S)-benzylidene-3-methyl-α-D-idopyranoside 
• 93-99-2 benzoic acid phenyl ester 

Downstream Products

• 1064194-70-2 [(2R,3R,4S,5R,6S)-4,5,6-Trimethoxy-3-(phenyl-phenylsulfanyl-methoxy)-tetrahydro-pyran-2-yl]-methanol 
• 51517-51-2 methyl 6-O-benzoyl-2,3-di-O-methyl-α-D-glucopyranoside 
• 56543-16-9 methyl 4-O-benzoyl-2,3-di-O-methyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 10227-29-9 methyl 2,3-di-O-methyl-α-D-glucopyranoside 
• 53437-96-0 Benzoic acid (2R,3S,4S,5R,6S)-3-hydroxy-4,5,6-trimethoxy-tetrahydro-pyran-2-ylmethyl ester 
• 120104-39-4 Benzoic acid (2R,3S,4S,5R,6S)-2-hydroxymethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester 
• 106220-89-7 methyl 6-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside 
• 83075-53-0 methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside 
• 178319-42-1 methyl 4-O-benzyl-2,3,6-tri-O-methyl-α-D-glucopyranoside 
• 196801-96-4 methyl 4-O-benzyl-2,3-di-O-methyl-6-O-triphenylmethyl-α-D-glucopyranoside 
• 27299-03-2 methyl 2,3-di-O-methyl-6-O-triphenylmethyl-α-D-galactopyranoside 
• 51433-19-3 methyl 4-O-benzyl-2,3-di-O-methyl-α-D-galactopyranoside 
• 74334-92-2 methyl 4-O-benzyl-2,3,6-tri-O-methyl-α-D-galactopyranoside 

Relevant articles and documents

Reconciling solvent effects on rotamer populations in carbohydrates - A joint MD and NMR analysis

The rotational preferences of the hydroxymethyl group in pyranosides is known to depend on the local environment, whether in solid, solution, or gas phase. By combining molecular dynamics (MD) simulations with NMR spectroscopy the rotational preferences for the ω angle in methyl 2,3-di-O-methyl- α-D-glucopyranoside (3) and methyl 2,3-di-O-methyl-α-D- galactopyranoside (6) in a variety of solvents, with polarities ranging from 80 to 2.3 D have been determined. The effects of solvent polarity on intramolecular hydrogen bonding have been identified and quantified. In water, the internal hydrogen bonding networks are disrupted by competition with hydrogen bonds to the solvent. When the internal hydrogen bonds are differentially disrupted, the rotamer populations associated with the ω angle may be altered. In the case of 3 in water, the preferential disruption of the interaction between HO6 and O4 destabilizes the tg rotamer, leading to the observed preference for gauche rotamers. Without the hydrogen bond enhancement offered by a low polarity environment, both 3 and 6 display rotamer populations that are consistent with expectations based on the minimization of repulsive intramolecular oxygen-oxygen interactions. In a low polarity environment, HO6 prefers to interact with O4, however, in water these interactions are markedly weakened, indicating that HO6 acts as a hydrogen bond donor to water.

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.

Compositions and methods for modification of biomolecules

The present invention provides modified cycloalkyne compounds; and method of use of such compounds in modifying biomolecules. The present invention features a cycloaddition reaction that can be carried out under physiological conditions. In general, the invention involves reacting a modified cycloalkyne with an azide moiety on a target biomolecule, generating a covalently modified biomolecule. The selectivity of the reaction and its compatibility with aqueous environments provide for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).