97232-16-1

Usage

Uses

Used in Pharmaceutical and Chemical Industries:
4,6-O-Benzylidene-D-glucopyranose is used as a building block for the synthesis of novel carbohydrate-based materials, leveraging its unique structural and reactivity properties to create innovative compounds with potential applications in drug development and other chemical processes.
Used in Drug Delivery Systems:
4,6-O-Benzylidene-D-glucopyranose is utilized as a component in the design and development of drug delivery systems. Its unique structure allows for the creation of systems that can improve the efficacy and targeted delivery of therapeutic agents, potentially enhancing the performance of drugs in treating various diseases and conditions.

InChI:InChI=1/C13H16O6/c14-9-10(15)12(16)18-8-6-17-13(19-11(8)9)7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8?,9-,10?,11-,12?,13?/m1/s1

Upstream product

• 492-62-6 alpha-D-glucopyranose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 
• 59-23-4 D-Galactose 
• 100-52-7 benzaldehyde 
• 10257-28-0 D-Galactose 
• 530-26-7 D-Mannose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 1269490-06-3 N,O-dimethyl-N-(4,6-O-benzylidene-β-D-glucopyranosyl)hydroxylamine 
• 113533-74-7 (2R,4aR,7R,8R,8aS)-6-Pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 

Downstream Products

• 257925-66-9 acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside 
• 60618-81-7 1,2,3-tri-O-acetyl-4,6-O-benzylidene-β-D-glucopyranose 
• 65987-12-4 1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 84276-56-2 allyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 111271-25-1 2-(3',5'-O-Benzylidene-D-gluco-pentahydroxypentyl)thiazolidine 
• 784179-19-7 benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-α,β-D-glucopyranoside 
• 175980-93-5 (2S,4aR,6S,7R,8R,8aR)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 

Relevant academic research and scientific papers

Synthesis of photolabile group protected anomeric acetals and its application in carbohydrate synthesis with the assistance of continuous flow photo-reactor

Selective deprotection of photolabile anomeric 2-nitrobenzyl acetals was achieved using continuous flow photo-reactor (UV radiation at 355 nm) in methanol-water. Various protecting groups such as acetyl, benzyl, benzoyl, benzylidine, TBS, etc. were found to be highly stable during the photolysis.

An Improved, Versatile, and Easily Scalable Synthesis of Sphingomyelins: Application to Stable Isotope Labeling

With a view to make conveniently labeled mass spectrometry standards available, a set of deuterated sphingomyelins were prepared by a new expedient, flexible, robust, scalable, and high-yielding synthetic scheme starting from 2-azido-3- O -benzoylsphingos

NATURAL AND SYNTHETIC DITERPENE GLYCOSIDES, COMPOSITIONS AND METHODS

Novel diterpene glycosides isolated from Stevia extract as well as diterpene glycosides that are synthetically prepared are provided herein. Compositions and consumables comprising the novel diterpene glycosides are also provided herein. Methods of enhancing the sweetness and/or flavor of consumables using the novel diterpene glycosides, methods of preparing compositions and consumables comprising the novel diterpene glycosides, methods of purifying the novel diterpene glycosides and methods of synthesizing the diterpene glycosides are also provided.

Oligosaccharide compound and its manufacture and its intermediate

The purpose of the present invention is to provide an oligosaccharide with high versatility that can produce a protected sulfate oligosaccharide that can become a manufacturing intermediate of polysulfated hyaluronic acid, and to provide a manufacturing method therefor and an intermediate thereof. Position 2 amino groups in glucosamine, galactosamine, and the like can react with saccharide receptors having an electron attracting group such as glucuronic acid and protected sulfate groups, by using a saccharide donor protected by a specific protective group.

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

Synthesis of an allergy inducing tetrasaccharide “4P-X”

4P-X (β-D-galactopyranosyl-(1?→?4)-β-D-galactopyranosyl-(1?→?6)-[β-D-galactopyranosyl-(1?→?4)]-β-D-glucopyranose) is included in galacto-oligosaccharides (GOSs) produced by β-galactosidase derived from Bacillus circulans. 4P-X has been known to induce particularly strong allergies. High purity 4P-X is essential for use as a standard to quantify the amount of 4P-X in GOSs; however, the isolation of high purity 4P-X has never been reported. In this study, we achieved the synthesis of 4P-X by a combination of organic and enzymatic chemical syntheses in a short time. This is the first report of isolated, high purity 4P-X.

Α - galactose ceramide new isomer and its synthetic method

The invention provides an alpha-galactosyl ceramide new isomer and its synthetic method. Configuration of sphingosine chain is changed to 4,5-cis double bond sphingosine chain. According to the invention, reaction steps are shortened, yield is raised, and aftertreatment and purification steps are omitted. The synthetic method can be used for total synthesis of similar glycosyl ceramide and satisfies wide range of development, research and application of different glycosyl ceramide.

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 Monoesterification Study of the Diol in 1-C-(4,6-O-Benzylidene-β-D-glucopyranosyl) Acetone

1-C-(4,6-O-Benzylidene-β-D-glucopyranosyl) acetone has been studied in a catalytic system consisting of triethylamine-p-dimethylaminopyridine (TEA-DMAP) in the presence of a number of esterification reagents in dichloromethane. It was found that all-protected and monoprotected products form simultaneously. However, the regioselectivity tends to favor the 3-substituted derivative. Structural parameters have been determined by 1H NMR, 13C NMR, 1H-1H correlation spectroscopy, and elemental analysis. Furthermore, a possible mechanism for the formation of intramolecular hydrogen-bond networks between the carbonyl group and 2-OH was described. The energy changes of the transition state in this reaction, as determined by a molecular modelling study, provided further evidence to assign the relative reactivities of each individual hydroxyl group.

4,5-Cis Unsaturated α-GalCer Analogues Distinctly Lead to CD1d-Mediated Th1-Biased NKT Cell Responses

The total synthesis of 4,5-cis unsaturated α-GalCer analogues was achieved, and their immune-response altering activity was assessed in vitro as well as in vivo in mice. Using glycosyl iodide as a glycosyl donor, construction of the sphingosine unit was shortened by four steps and single α-stereoselectivity was achieved in good yield (67%). With regard to the therapeutic use of α-GalCer, the novel analogues (1b and 1c) distinctly induced a Th1-biased cytokine response, avoiding induction of a contradictory response and overstimulation.