14581-89-6

Basic information

• Product Name: b-Naphthyl b-D-Glucopyranoside Tetraacetate
• Synonyms: 2-Naphthalenyl b-D-Glucopyranoside Tetraacetate;2-Naphthyl b-D-Glucopyranoside Tetraacetat;b-Naphthyl b-D-Glucopyranoside Tetraacetate;2-Naphthalenyl -D-Glucopyranoside Tetraacetate;2-Naphthyl -D-Glucopyranoside Tetraacetate;-Naphthyl -D-Glucopyranoside Tetraacetate;2-Naphthyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside;b-Naphthyl β-D-Glucopyranoside Tetraacetate
• CAS NO: 14581-89-6
• Molecular Formula: C₂₄H₂₆O₁₀
• Molecular Weight: 474.46
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates & Derivatives
• Mol File: 14581-89-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 198-199℃ (benzene )
• Appearance: /
• Refractive Index: 1.568
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: b-Naphthyl b-D-Glucopyranoside Tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: b-Naphthyl b-D-Glucopyranoside Tetraacetate(14581-89-6)
• EPA Substance Registry System: b-Naphthyl b-D-Glucopyranoside Tetraacetate(14581-89-6)

Safety Data

• Hazardous Substances Data: 14581-89-6(Hazardous Substances Data)

Usage

Description

β-Naphthyl β-D-Glucopyranoside Tetraacetate, with the CAS number 14581-89-6, is a synthetic compound that plays a significant role in the field of organic synthesis. It is characterized by its unique chemical structure, which allows it to be utilized in various chemical reactions and processes.

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

• 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 
• 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 

Downstream Products

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

Relevant articles and documents

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.

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.

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.