30688-66-5

Usage

Uses

Used in Pharmaceutical Industry:
4,6-O-Benzylidene-D-glucose is used as a key intermediate for the synthesis of various pharmaceutical compounds, particularly those with carbohydrate moieties. Its unique structure allows for the development of novel drugs with improved bioavailability, targeting, and efficacy.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4,6-O-benzylidene-D-glucose is utilized as a starting material for the preparation of a wide range of complex carbohydrates, glycosides, and other carbohydrate-derived compounds. Its benzylidene protection group can be selectively removed under mild conditions, facilitating the introduction of various functional groups and the construction of diverse molecular architectures.
Used in Research and Development:
4,6-O-Benzylidene-D-glucose is also employed in research and development for the study of carbohydrate chemistry, biochemistry, and molecular biology. It serves as a model compound for understanding the structure, function, and interactions of carbohydrates in biological systems, as well as for the development of new methods and techniques in carbohydrate synthesis and analysis.
Used in Material Science:
In material science, 4,6-O-benzylidene-D-glucose can be used as a component in the design and synthesis of carbohydrate-based materials, such as polymers, gels, and nanoparticles. These materials have potential applications in various fields, including drug delivery, sensors, and biocompatible coatings.

InChI:InChI=1/C13H16O6/c14-6-9(15)11(17)12-10(16)7-18-13(19-12)8-4-2-1-3-5-8/h1-6,9-13,15-17H,7H2/t9-,10+,11+,12+,13?/m0/s1

Upstream product

• 2280-44-6 D-Glucose 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 50-99-7 D-glucose 
• 492-62-6 alpha-D-glucopyranose 

Downstream Products

• 65987-12-4 1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 84276-56-2 allyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 784179-19-7 benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-α,β-D-glucopyranoside 
• 108257-55-2 1,2,3,4-tetra-O-acetyl-6-O-benzyl-β-D-glucopyranose 
• 108257-52-9 1,2,3,4-tetra-O-acetyl-6-O-benzyl-α-D-glucopyranose 

Relevant academic research and scientific papers

METHOD OF PRODUCING GALACTOOLIGOSACCHARIDE, AND INTERMEDIATE THEREOF

PROBLEM TO BE SOLVED: To provide a method of producing a galactooligosaccharide that may cause the onset of allergic reaction, and an intermediate thereof. SOLUTION: A method of producing a galactooligosaccharide represented by the general formula (1) comprises addition of the 1-position of protected galactobiose to the 6-position hydroxy group of protected lactose of formula (5), and subsequent deprotection of a hydroxy group protecting group. SELECTED DRAWING: Figure 5 COPYRIGHT: (C)2018,JPOandINPIT

Tertiary Amine Promoted Asymmetric Aldol Reaction of Aldehydes

The direct asymmetric self-aldol reactions of various α-oxyaldehydes catalyzed by tertiary amines have been demonstrated. By using 10 mol-% of quinine catalyst, dimerization products have been prepared in high yields, with good anti-diastereocontrol, and up to 80% ee. The presented enolate-mediated synthesis of protected tetrose sugars has never been accomplished before by chiral tertiary amine organocatalysts.

Regioselective removal of the anomeric O-benzyl from differentially protected carbohydrates

A mild, regioselective deprotection of the anomeric O-benzyl from multi-functionally protected carbohydrates via catalytic transfer hydrogenation is described. The protocol is tolerant of O-benzyl and O-benzylidene protections at non-anomeric positions, g

Involvement of the S-aglycon in the conformational preferences of thioglucosides

The conformational preferences of two series of alkyl β-d-thioglucopyranosides in solution were investigated by NMR and CD. The rotamer populations of the hydroxymethyl group were found to depend on the structural nature of the S-aglycon. The population of the gt rotamer increased and that of the gg rotamer decreased as the alkyl group attached to the S atom increased in size. These rotamer populations have a linear correlation with the Taft' steric parameters, the nS s(-) σC s(-) O* exo-anomeric interaction may express these rotational preferences. Comparative analysis of the hydroxymethyl populations between alkyl O- and S-glucosides revealed identical or slightly higher gt and smaller gg populations for the latter compounds.

Inhibitory effects of Ellagi- and gallotannins on rat intestinal α-glucosidase complexes

The clove ellagitannins and their related polygalloylglucoses inhibited maltase activity of rat intestinal α-glucosidases. The structure-activity relationship study of those galloylglucoses, varying the extent of galloylation on the glucose core, with the

The reaction of partially protected aldoses with stabilized arsonium ylides: Synthesis of E acyclic unsaturated derivatives and C-glycosyl derivatives

The reaction of partially protected aldoses with (carbomethoxymethyl)triphenylarsonium bromide and zinc in toluene gave E α,β-unsaturated acyclic esters. When intramolecular transesterification occurred, bicyclic 1,4-lactone derivatives were formed concurrently. Otherwise, using these non alcaline conditions, olefination did not favour the formation of C-glycosyl derivatives. On the other hand, when the reaction was performed with (carbomethoxymethylene)triphenylarsorane in toluene, followed by the addition of n-butyllithium, bicyclic derivatives were obtained rapidly in good yields. Moreover, when cyanomethyltriphenylarsonium bromide was used in place of (carbomethoxymethyl)triphenylarsonium bromide, the corresponding E aldooctenonitriles were produced in satisfactory yields.

A new approach to some 1,6-dideoxy 1,6-epithio sugars

The treatment of hexopyranosyl bromides, also activated at C6 (Br, OTs, OMs), with H2S/HCONMe2 under basic conditions gives rise to 1,6-dideoxy 1,6-epithio sugars. One such sugar has been further transformed into the synthetically useful 3,4-anhydro-1,6-dideoxy-1,6-epithio-β-D-galactose. The treatment of this epoxide with sodium azide and with cyclohexylamine is described. An analogous treatment of one doubly activated hexopyranosyl bromide with sodium hydrogen selenide has led to a novel 1,6-dideoxy 1,6-episeleno sugar which displayed interesting n.m.r. spectra. Finally, in an attempt to prepare 1,6-dideoxy 1,6-epidithio sugars, a tetraalkylammonium tetrathiomolybdate reagent was found to be the reagent of choice for converting doubly activated hexopyranosyl bromides into 1,6-dideoxy 1,6-epithio sugars.

CD and 1H NMR Study of the Rotational Population Dependence of the Hydroxymethyl Group in β Glucopyranosides on the Aglycon and Its Absolute Configuration

The rotamer population around the C5-C6 bond of chiral and nonchiral alkyl β-glucopyranoside derivatives proved to be dependent on the structure of the aglycon; the population of the gg and gt rotamers decreased and increased, respectively, as the pK