14581-89-6

Usage

Uses

Used in Organic Synthesis:
β-Naphthyl β-D-Glucopyranoside Tetraacetate is used as a synthetic intermediate for the production of various organic compounds. Its versatile chemical structure makes it a valuable building block in the synthesis of complex molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, β-Naphthyl β-D-Glucopyranoside Tetraacetate is used as a key component in the development of new drugs. Its unique properties enable it to be incorporated into the molecular structure of potential therapeutic agents, contributing to their overall efficacy and safety.
Used in Research and Development:
β-Naphthyl β-D-Glucopyranoside Tetraacetate is also employed in research and development laboratories, where it is used to study the properties and behavior of various organic compounds. Its use in this context helps scientists gain a deeper understanding of chemical reactions and processes, ultimately leading to the discovery of new compounds and materials with potential applications in various industries.

InChI:InChI=1/C24H26O10/c1-13(25)29-12-20-21(30-14(2)26)22(31-15(3)27)23(32-16(4)28)24(34-20)33-19-10-9-17-7-5-6-8-18(17)11-19/h5-11,20-24H,12H2,1-4H3/t20?,21-,22+,23+,24-/m1/s1

Upstream product

• 135-19-3 β-naphthol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 18081-08-8 2-naphthyl trimethylsilyl ether 
• 89825-07-0 1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside 
• 83-87-4 D-glucose pentaacetate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 32316-92-0 naphthalene-2-boronic acid 

Downstream Products

• 6044-30-0 naphthyl-beta-D-glucopyranoside 

Relevant academic research and scientific papers

Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature

Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.

Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions

We report the efficient O-glycosidation of glycosyl bromides with therapeutically relevant acceptors facilitated by silver N-heterocyclic carbene (Ag-NHC) complexes. A set of four Ag-NHC complexes was synthesized and evaluated as promoters for glycosidation reactions. Two new bis-Ag-NHC complexes derived from ionic liquids 1-benzyl-3-methyl-1H-imidazolium chloride and 1-(2-methoxyethyl)-3-methylimidazolium chloride were found to efficiently promote glycosidation, whereas known mono-Ag complexes of 1,3-bis(2,4,6- trimethylphenyl)imidazolium chloride and 1,3-bis(2,6-di-isopropylphenyl) imidazolium chloride failed to facilitate the reaction. The structures of the promoters were established by X-ray crystallography and these complexes were employed in the glycosidation of different glycosyl bromide donors with biologically valuable acceptors, such as estrone, estradiol, and various flavones. The products were obtained in yields considered good to excellent, and all reactions were highly selective for the β isomer regardless of neighboring group effects.

On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2

Subtilisin-catalyzed esterification of several enatiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated.

Solid-liquid phase transfer catalyzed novel glycosylation reaction of phenols

A facile and mild glycosylation reaction in solid-liquid two-phase system (powdered K2CO3/CHCl3) containing phase transfer catalyst was found to be efficient for preparation of glucosides of 2', 6'-dihydroxyacetophenone (1) and other various substituted phenols.

Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride-diethyl ether as catalyst

Stereospecific formation of aryl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosides was achieved by reaction of penta-O-acetyl-β-D-glucose 1 with substituted phenols in the presence of boron trifluoride. Yields of the purified products varied from 52-85%. Benzyl alcohol could also be glucosylated using similar conditions. All products were purified by crystallization from ethanol. The purity and the anomeric configuration of the products were determined by means of 1H and 13C NMR spectroscopy, melting points and optical rotation.

Non-amphiphilic carbohydrate liquid crystals containing an intact monosaccharide moiety

A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R′ on the 4,6-O-ylidene β-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R′ for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.

Glycosides. Part 1. New Synthesis of 1,2-trans O-Aryl Glycosides, via Tributyltin Phenoxides

A new method of glycosidation of phenols has been studied.The reaction of tributyltin phenoxides 2 with 1,2,3,4,6-penta-O-acetyl-D-hexopyranosides 3, 7 and 9, in the presence of tin tetrachloride is described.Glycosides 4, 8 and 10 have been isolated in g

EINFACHE UND STEREOSELEKTIVE SYNTHESE VON α- UND β-PHENYLGLYKOSIDEN

Reaction of phenyl-trimethylsilylethers (3) with 1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside (1) (anomeric mixture) yields almost exclusively the aryl-β-glucosides (4) in the presence of catalytic amounts of TMS-triflate at 20 deg C, whereas (3)